The Duality of Blair Waldorf

Originally published on Substack 6/3-6/4/2021

[This profile contains discussion of eating disorders, abuse, and sexual assault.]

When I arranged the order of these profiles, I knew that Blair Waldorf’s would go last. She wouldn’t have it any other way. Not only is Blair the show’s most beloved character (type her name into YouTube and take in all the video compilations of her “best” or “most iconic” moments) but she’s also its most fashion conscious. The daughter of a designer, Blair speaks in fashion references and metaphors. “Fashion is the most powerful art there is,” she tells Dan Humphrey in season four. “It’s movement, design, and architecture all in one.”

Why is Blair so adored by viewers? I think the answer lies in her duality: she is both aspirational and relatable, perfect and flawed. She is rich, witty, beautiful, smart, thin; she has a bevy of handsome love interests. She is also deeply insecure, often jealous or scheming or cruel. She can be racist and classist and misogynist. (To quote one of the stars of the Gossip Girl reboot, Evan Mock: “Blair was a white girl boss who had these little minions, and they’re people of color, Asian” (Vanity Fair).)

Her central conflict—and certainly the focus of her costume design—is this war between her “good” or “light” or “sparkly” side and her “bad” or “dark” side. (Light-and-dark dualism is, of course, not unique to this show; many English metaphors enforce the racist idea of lightness or whiteness as good and darkness or blackness as bad.)

Blair’s “good” side is highly controlled: “a very meticulous, thought-out way of being,” as head costume designer Eric Daman puts it (Fashionista). She buttons her ruffled white blouses to the hilt, tops with them with tight bows and pearl necklaces and regal headbands or capes—all ways that she asserts her power and status. She is always “appropriate” (“Gossip Girl Couture”), dressed perfectly for the occasion, whether it be a brunch or a masked ball or a wedding. And yet, underneath, in private, she favors sheer robes and slips and lingerie sets; for Blair, her “bad” side always means her sexuality—a loss of control. Throughout the series, Blair tries to reconcile these two parts to create a better, whole self—and no surprise, fashion always plays an important role. 

Season One

We first see Blair in a black dress with long lace sleeves and a black bow headband, black stockings and garters, and jet earrings. She’s at a party at the Waldorf penthouse, and she’s just learned that her best friend, Serena van der Woodsen, is back in the city.

The dress, we soon discover, is an Eleanor Waldorf original: “Tell me if you’re going to wear one of my designs,” Eleanor says to Blair, “so we can at least get it properly fitted.” This line is our first hint at the strained relationship between mother and daughter, and how that relationship fuels Blair’s insecurities, most especially about her body.

And yet, the black dress is a perfect first look at Blair; as I rewatched the series, I realized that Blair often chooses a black dress—usually paired with something sparkly, be it a necklace, neckline, or belt—for a formal occasion. The influence, I think, is her idol, Audrey Hepburn. After all, Audrey’s most iconic look is the black dress and sparkly accessories from the opening scene of Breakfast at Tiffany’s. For Blair, a black dress symbolizes style, elegance, grace, sophistication—everything Audrey embodies for her, everything she aspires to be. 

Blair pulls her boyfriend, Nate Archibald, into her bedroom; she wants them to have sex for the first time before he finds out Serena is back. Sex, in Blair’s mind, is the only way to keep Nate from her more experienced friend; waiting for sex was once a form of control, and now not waiting is.

Nate overhears Serena’s arrival before he and Blair can have sex. The disappointed Blair must zip up her dress and fake an excited hello for Serena. She’s angry at her friend for going away to boarding school without telling her, for not being there during the Waldorfs’ messy divorce. The next day at school, Blair reluctantly agrees to a drink with Serena.

On the Met steps, where Blair and her minions reign, we get our first look at Blair’s uniform: a ruffled white blouse, navy blazer and crossover tie, white tights, and yellow headband, all with the junior class’s standard navy kilt. As queen of Constance Billard School for Girls, Blair favors preppy pieces with a regal air: the high-necked blouse like an Elizabethan ruff, the headband like a “crown” (“Couture”). Her minions, like a royal court, all copy elements of her look: headbands, white blouses, and white knee-high socks or stockings. The overall effect is one of unity and restraint, in contrast with the lone Serena; Blair and her minions never miss a button on their blouses, never unfasten their ties, but Serena wears her collar unbuttoned, her necktie loose, and with freshman year’s outgrown skirt.

That evening, Blair and Serena reconcile over martinis, then Blair leaves to finish what she started with Nate. In her bedroom, she surprises him in a pink baby-doll slip with black trim and black stockings—not unlike the ones she wore to the party. This is the other side of Blair Waldorf, the one under the buttoned-up blouses and ties, the one who wants to be sexual and sexy. Instead, Nate tells Blair why Serena ran away to boarding school: she and Nate slept together.

Blair is heartbroken, but she agrees to put the incident behind them after Nate promises never to see Serena. They’re going to attend the Kiss on the Lips party together, and Serena is not invited.

Eleanor has laid out a dress for her daughter, but Blair tries on this one instead: a silky purple gown with a sequined drop waist. It’s more sexy and formfitting than any outfit we’ve seen her in, and so Eleanor immediately rejects it: “This [dress] is not as elegant a choice as that one. Blair, you’ll never be more beautiful or thin or happy than you are right now.”

In her mother’s words, we hear many of Blair’s internalized ideas: that to be elegant is not to be sexy, that to be beautiful and thin is to be happy. It’s no surprise that Blair wears the other dress to the party, a black dress—paired with drop pearl earrings.

The next morning (1.2), Blair’s mother has left her a blue strapless Waldorf Designs dress, a note paper-clipped to it: “Went to Paris. [Bass] Brunch at 2. Wear pearls!” Blair discards the dress, giving it to an aspiring minion, Jenny Humphrey. “[The dress is] average,” she tells Jenny. “The color is last season. And besides, Stella McCartney has a much better version at Bergdorf’s.” Blair is incredibly knowledgeable about her mother’s high-fashion world, even if it’s at the expense of her mother’s own designs.

Serena visits before the brunch; she wants to pick up their Sunday morning tradition of watching Breakfast at Tiffany’s and eating croissants—a tradition likely invented by Blair. Blair rejects the plan, telling Serena that she knows she slept with Nate, that she always took Serena for a “slut” but not a “liar” too.

Naturally, Blair chooses virginal white for brunch: a white eyelet dress with a big bow at the waist, along with a navy bow headband, her signature ruby ring, and, what else, a little pearl bracelet. Though she may have tossed aside her mother’s dress, she can’t rebel completely.

After Blair finds Nate talking with Serena—as he promised he wouldn’t—her fury only increases: she tells Serena’s new love interest, Dan, why Serena ran away; she tells their school’s Ivy League mixer that Serena is being treated for addiction at the Ostroff Center (1.3).

Blair wants nothing more than to go to Yale, like her beloved father: “Do you remember when Dad gave me my first Yale sweatshirt?” she asks her maid and surrogate mother, Dorota (who, I should note, wears a headband as part of her uniform). “I don’t think any piece of clothing has ever fit me more perfectly.” In preparation for the mixer, the junior class attends an assembly, and Blair is pressed and coordinated, as usual: a white ruffled blouse, white headband, and red tights with her uniform skirt. And as if one bow isn’t enough, her crossover tie has a bow brooch pinned on top. Bows are already a motif for Blair—feminine, preppy, but also controlled, never undone, much like Blair herself. Even her clothing hangers are festooned with little bows.

To the mixer itself, Blair wears a navy skirt suit, a yellow blouse with a brooch at the collar, and a pearl necklace; her hair in a bun. Her look is the most serious, least fashionable, that we’ve seen yet: closer in style to the Ivy League recruiters than her fellow students. The more Blair grasps at control—at securing admission to Yale, at defeating Serena—the more severe, conservative, her wardrobe gets.

After Blair learns that Serena is not a patient at the center—her brother, Eric van der Woodsen, is—she and Serena make up. Still, even in friendship, the threat of Serena—her beauty, her charisma, her ease—lurks. In episode four, we see our first Blair dream sequence, one of many throughout the series. Blair dreams in Hollywood movies, often taking the place of her favorite star, Audrey Hepburn.

In this dream, Blair is Holly Golightly in the opening scene of Tiffany’s: a black dress and opera gloves, piles of pearl necklaces and bracelets, a little crown, and black sunglasses. Blair approaches the store window, only to see it’s Henri Bendel’s, not Tiffany’s, and Serena is inside, Blair’s minions serving her. Dream Serena is wearing the same outfit Blair wore when Serena returned to the city: a black headband and black lace dress. In Blair’s mind, Serena is replacing Blair in her mother’s affections, all while wearing the dress that Eleanor said didn’t fit Blair properly.

Blair wakes to find her mother and Serena eating breakfast. Bendel’s, says Eleanor, is interested in carrying Waldorf Designs. Blair reaches for a croissant, the same pastry she carried in her dream, but her mother suggests she try the “low-fat yogurt” instead. (Serena, halfway through her own croissant, receives no such admonishment.) Even shamed, Blair still wants to please her mother: “I lost two pounds while you were away.”

With Serena’s encouragement, Blair agrees to be the face of the new Bendel’s line. She has trouble, however, posing for the campaign’s test shots. She is too “prim and stiff, like a bookcase,” the photographer mutters. “How is the client going to like the dress if the model doesn’t even like herself?” After overhearing the photographer, Serena helps Blair loosen up, offering her directions. Indeed, Blair’s test-shot look is full of Serena hallmarks—the yellow-and-black color combination, sequins, short gloves—even if the dress’s and hat’s vintage silhouettes are very Blair. 

The photographer and director advise Eleanor to choose Serena instead, and Eleanor does—telling her daughter, the morning of the shoot, that they’ve gone in a “different direction.” Blair pretends not to care, but once her mother exits, she leaves Serena a voice mail; they should still go to the shoot, Blair says, and “make fun of the skinny bitch.”

Blair arrives on set to find that the “skinny bitch” is, in fact, Serena—who believed that she was doing the shoot with Blair. “You take everything from me!” Blair yells. “Nate, my mom. You can’t even help it. It’s who you are.” This is Blair at her most stripped-down: a simple forest-green shirtdress and a strand of pearls—and no headband, no power. By the end of the episode, Blair tells off her mother, and she and Serena make up.

In episode six, Blair even asks Serena to be one of her “handmaidens” at that evening’s masked ball. Blair has planned a scavenger hunt for Nate; throughout the night, he’ll receive clues to Blair’s location from her handmaidens, Serena delivering the final clue. If Nate finds Blair before midnight, they’ll sleep together for the first time. It’s exactly Blair’s kind of fantasy, a Cinderella-like romance, complete with fanciful costumes.

For the ball, Blair chooses a black gown, diamond tiara, and silver filigree mask on a handle—yet again, a black dress and something sparkly. The mask does little to disguise her appearance because Blair desperately wants Nate to find her. But Nate is still in love with Serena and tells her so—or at least he thinks he does, mistaking another tall blonde, Jenny, for Serena. At the end of the ball, a disappointed Blair goes home alone, her coach turned back into a pumpkin: “All I wanted was for us to start over,” she tells Nate, “and you didn’t even try.”

Blair’s hopes are raised and dashed again in episode seven: Eleanor has agreed to Nate’s father, Howard Archibald, taking her company public. To hasten the deal, Nate’s mother, Anne Archibald, says that Blair will receive her van der Bilt family diamond upon her and Nate’s engagement. When Eleanor delivers this news, Blair is wearing a green-and-white rugby shirt and her initial necklace, BW for Blair Waldorf. The shirt shows us how much Blair wants to make her relationship with Nate work—even dressing like him—while the initial necklace reminds us of the real reason Nate has been holding on to their relationship: his father’s deal with Waldorf Designs.

Eleanor presents Blair with a dress for their celebratory dinner with the Archibalds: “It would be very nice if I was sailing up on the Mayflower,” Blair quips. The dress is almost as conservative as Blair’s suit: high-necked gray-green lace, trimmed in black ribbon. Blair pairs it with a yellow headband and knotted pearl necklaces.

Before the dinner, however, Jenny tells Blair what happened with Nate, and the heartbroken Blair dismisses her as a minion. She and Nate break up at the dinner, and Blair goes somewhere where she knows she can escape: Chuck Bass’s burlesque club, the Victrola.

Chuck is Nate’s best friend, the lecherous son of real estate billionaire Bart Bass. He encourages Blair’s scheming, sexual side: her revenge against Serena, her plans to lose her virginity, and in this episode, her dance onstage at the Victrola.

Blair tosses her headband aside, then unzips her dress and lets it drop. Underneath is a cream silk slip; the “bad,” sexual counterpart to the “good,” puritan “Mayflower” dress. Her dance itself is fairly chaste—she mostly wiggles around in her slip, tossing her hair or playing with her pearls. But for Blair, her dance is a huge deal, a release of her repressed sexual feelings, not planned or perfect, wrapped in Cinderella or Hollywood fantasy. Later that night, in Chuck’s limo, Blair is still in her slip; there, they kiss and then sleep together.

The next morning (1.8), “good” Blair must repent for “bad” Blair’s choices. She attends confession in a black suit, gray shirt, and black tie; the pièce de résistance is a headband with a black net veil. (WASP-y Blair’s only Catholic fashion reference must be Jackie Kennedy’s funeral veil.) After confessing her “sin,” Blair pops off the headpiece and puts on her sunglasses. She’s off to the jeweler, where she’ll place pieces on hold for her seventeenth birthday, including an Erickson Beamon diamond necklace. Nate wants to get back together—his family hoping to save the Waldorf deal after Howard’s arrest—and Blair is convinced he picked up the necklace.

To her party, Blair wears a black cocktail dress with sheer sleeves and two silver-buckled belts—no jewelry yet, as she believes she’ll soon be wearing the necklace. Nate usually calls her at midnight on her birthday, but when 12:01 rolls around, Blair knows they’re broken up for good.

Chuck, meanwhile, has spent the episode suppressing his feelings for Blair by manipulating both her and Nate. Nate didn’t buy the necklace—Chuck did, and he presents it to Blair: “Something this beautiful deserves to be seen on someone worthy of its beauty.” It’s quite a line, but one that’s perfect for Blair. After being rejected, over and over, for other girls, she wants to be seen as beautiful, desirable—sparkly.

The next episode flashes back to the Thanksgiving before, when Serena was her old, wild self and Blair’s parents were together. Sophomore Blair’s wardrobe is much more juvenile than her current one; you can see just how much a year without her father or best friend aged her. In fact, her first outfit looks more like something freshman Jenny would wear: a purple turtleneck under a gray baby-doll jumper, a wide green headband, and a gray hooded plaid coat.

In the present day, Blair is dressed similarly: a high-waisted shirtdress and wide tweed headband, the oranges and browns perfect for the fall holiday. She believes her father, Harold Waldorf, is coming to Thanksgiving dinner, and so she has reverted back to her less mature wardrobe, his little girl again. After Eleanor informs Blair that Harold isn’t coming, she asks her daughter to change into “something a little more enchanting” for dinner.

Blair trades her shirtdress for a tan lace dress with white-and-black trim, tan headband, and pearl necklaces—all together, a lot like the Mayflower outfit that her mother picked out a few episodes ago, Eleanor’s idea of “enchanting.” Turns out Eleanor told Harold that Blair didn’t want to see him for the holiday, and when Blair confronts her mother at dinner, she realizes that Eleanor also sent Harold’s pumpkin pie—their Thanksgiving tradition—down to the doorman. Eleanor goads her daughter into choosing one of their caterer’s desserts instead; Blair selects an apple pie and takes it to their kitchen.

All the employees, even Dorota, leave the kitchen, as if they’ve seen this before and know exactly what’s about to happen. While Blair binges and purges, the scene flashes back to every bite of food she has taken on the show, to Blair purging in the bathroom after lunch with Nate in the pilot. As the show hinted but never confirmed before this episode, Blair has bulimia; as of the previous Thanksgiving, she had been in treatment for a few months. Luckily, Blair has the support of Serena, and she agrees to call her doctor the next day.

Throughout the rest of the series, Blair’s bulimia is largely mentioned in passing, when it’s convenient for the story line. In retrospect, I wish the show had spent more time reflecting on Blair’s eating disorder and how it ties into other aspects of her character, in her need for control and perfection. Through bulimia, Blair tries to assert control over her body, her life—much in the same way she uses fashion to craft a tidy, perfect picture. I sometimes wonder if Blair’s obsession with Audrey Hepburn is in part fueled by how thin Audrey was, and how much a part of her star image that was—“gamine” or “waiflike.” (In truth, Audrey was thin throughout her life because she was malnourished during World War II (People).)

By the next episode, Blair is breezy and carefree—so much so that Nate becomes interested in her again. Blair has continued secretly sleeping with Chuck (the gross implication, I suppose, is that sex has made her less uptight). She agrees to attend cotillion with Nate “as friends,” and then shows up to his tux fitting late. Suddenly, Nate is the try-hard and Blair is the careless one, dressed in a green suede jacket, brown sweater, and skinny jeans, no headband. Blair almost never wears jeans, or pants in general, so it’s surprising to see her so casual, more like Serena than Blair.

For cotillion itself, she’s back to Blair, her cool silver contrasting with Serena’s warm gold and coordinating perfectly with Nate’s gray. Her gown has a huge bow on one shoulder, Chuck’s necklace complementing its silver brocade. Chuck tries to stop Nate and Blair’s reunion, but he only drives them closer; at the end of the night, they sleep together for the first time, and Chuck runs away to Monaco.

In episode eleven, Blair’s father visits for Christmas, but he’s brought his boyfriend, Roman—the man he left Eleanor for. Just as she did at Thanksgiving, Blair reverts back to her “good,” younger self, the girl she was when her parents were together: For ice-skating in Central Park, she wears a gray plaid cape and skirt set, pink turtleneck, white tights, and white pom-pom hat and gloves. (She owns her own skates, of course, and has decorated them with little pink pom-poms.) For her mother’s Christmas party, a white-and-gold swingy dress and red velvet headband. The pink and white, the pom-poms, and the trapeze silhouette are all more immature, more Jenny-like, than anything she’s worn in the present day. Hell, she looks like a Samantha doll. Harold is surprised when Blair schemes to break him and Roman apart; he’s still looking at Blair pre-divorce.

Throughout the episode, Blair receives texts from Chuck: how did she fake her virginity for Nate, who would he tell about their fling—accompanied by a photo of him and Nate. The threat is implied and then spoken in episode twelve: Chuck wants Blair to stay away from Nate, or he’ll tell Nate about sleeping with Blair.

Blair avoids Nate, but he keeps trying to win her back. He writes her a love letter, even attempts to take the blame for breaking into the school pool—the “most romantic thing” anyone has ever done for Blair. In the end, she asks Nate if they can forgive and forget their past, and he assures her that “nothing” can tear them apart.

Well, not quite nothing. In episode thirteen, Blair’s period is late and she’s in denial. “Whenever something happens that’s not a part of your plan,” says Serena, “you pretend like it doesn’t exist. You act like you’re in this movie about your perfect life, and then I have to remind you that the only one watching that movie is you.” Though the pregnancy test Serena buys for Blair comes back negative, the real horror movie is only just beginning.

Angry that Blair is no longer beholden to his wrath, Chuck sends a tip to Gossip Girl: Blair slept with two guys in the same week. The slut-shaming is immediate, both at school and in the blogosphere. As Gossip Girl writes, “Looks like the virgin queen isn’t as pure as she pretended to be. . . . Two guys in one week? Talk about doing the nasty. Or should I just say, being nasty?”

When the post drops, Blair is dressed in a very uncharacteristic color combination. Usually she favors blues, reds, and whites with her uniform—blue being the color of her now ex, Nate; red, the color of her signature ring. Instead, she is wearing the opposites of blue and red on the color wheel, discordant orange and green: a green jacket and headband, an orange blazer—and bright white tights, perhaps symbolizing the virginal expectations she had for herself. As she tells Serena later that day, “The rules are different for the Serena van der Woodsens of the world. People expect you to party and be wild, sleep with whoever you want, run away, come back.”

The next day, her color palette is still off: red tweed coat, green-and-red striped headband, clip-on gold bow, tights, and button-down. Blair rarely wears gold, because it isn’t her color, it’s Serena’s—a symbol of her friend’s desirability, but also, in this case, her sexual history. We see nothing of Blair’s actual uniform—her coat buttoned to cover her skirt, her crossover tie gone, all signs of her impending dethronement as Constance’s queen. Her former minions declare Blair a “hypocrite”; she judges others for their sexual pasts but expects leniency for her own. Even Chuck rejects her, telling her that she was desirable only when she was “untouched.”

At home, Blair begs her mother to send her to boarding school in France—like Serena, running away to boarding school; like her father, running away to France. She’s completely undone, the headband she was wearing earlier gone. Only Serena stops Blair from getting on the plane: “Don’t let some stupid scandal make you run away, like it did me,” says Serena.

Blair returns to school the following episode in a matronly blue coat, printed kerchief, and sunglasses; she’s afraid to be seen as a young, sexual being. Serena convinces Blair that her scandal has blown over, and Blair reluctantly removes the sunglasses and kerchief—no headband underneath. By the time they reach school, however, the whispers have started; her former minion, Jenny, even drops a spoonful of yogurt on Blair’s head. Funnily enough, if Blair had kept on the scarf, her hair would’ve been protected.

Blair tries to win her minions back, but Jenny proves a tougher adversary than Blair anticipated. She begins to regain her power in episode fifteen, when she enlists her minions in taking down Nelly Yuki, the most accomplished student at Constance and their rival for the best SAT score and Ivy League admission. Suddenly, Blair is back in blues, reds, and whites—and headbands.

Blair finally humiliates Jenny at a party, in the most fuck-you dress: black and flapper-esque, with a silver, almost bow-like neckline. Again, Blair chooses a black dress with sparkle for a big moment, but as I noted in Jenny’s profile, the more interesting detail is her long pearl necklace, the ends encircling her wrists. If she pulls too hard, she’ll choke her own neck—the power you wield often hurts you the most.

“I tried to warn you,” she tells Jenny, teary-eyed. “There’s a price to pay.” It’s almost as if she’s looking back at her younger self, her regrets. What price have you paid, B?

Blair spends the next couple episodes taking down Serena’s old frenemy, Georgina. Her schemes bring her closer to her favorite scheming partner, Chuck, and they reunite at his father’s wedding, Blair’s pink floral dress and headband matching his pink floral bowtie. As she later tells Serena, “He brings out the worst in me. And weirdly, I think I bring out the best in him.”

Blair is spending the summer in Tuscany with Chuck and France with Harold and Roman. She heads to the Bass jet in a navy sailor-like dress, white belt, and white net gloves, a little green kerchief knotted at the neck—all ready to “set sail” for Europe. Chuck, however, isn’t prepared for the commitment that such a vacation might bring, and he abandons her on the tarmac.

Season Two

Blair returns from Europe with a new beau, James. For her end of the summer in the Hamptons, she favors brightly colored floral dresses, headbands, and one-piece swimsuits, often worn with her initial or nameplate necklaces. She’s only dating James to make Chuck jealous, faking the “bloom” of her love with floral prints; she becomes genuinely interested in James when he reveals that his real name is Lord Marcus Beaton, and he’s the son of a British duke.

Chuck, unable to say “I love you,” can’t compete with real live royalty. Blair adores Roman Holiday, Grace Kelly, even Marie Antoinette—the subject of the mural in her bedroom. She wants to impress Marcus’s stepmother, the duchess, and throws a staid party complete with classical music (2.2). She even wears her Waldorf nameplate necklace with her cream-and-black floral strapless dress and pearl headband. Blair’s name means a lot in New York circles, but it’s not enough to impress Duchess Catherine: “Marcus is never going to end up with a lowly Waldorf,” she says.

Blair blackmails the duchess into approval, but her relationship with Marcus is still lacking. They haven’t had sex, despite Blair’s urging. When she references the library scene in Atonement, Marcus replies, “Blair, that’s not you. You’re a delicate little flower, nothing like that tart Keira Knightley” (2.3). Marcus’s framing of Blair as a “delicate little flower” not only calls back to all the florals she wore at the beginning of their relationship but also reinforces Blair’s ideas about her sexual desires—that they’re something depraved and dirty, nothing to be encouraged.

Chuck, meanwhile, decides to use sex with Blair to end a streak of impotence. He has always been fascinated, he says, by Blair’s “cool exterior and the fire below”—her “good,” restrained side and her “bad,” sexual one. The problem is, Marcus wants only the former and Chuck wants only the latter.

Chuck tries to seduce Blair at her back-to-school party, even pretends to be Marcus in the dark of a city-wide blackout. Blair wears a yellow one-shouldered Grecian-like dress and gold headband—again, wearing yellow and gold, like Serena, when her sexual history is being used against her.

After Marcus discovers Chuck and Blair kissing, Blair is finally able to ask for what she wants: “I’m not some delicate little flower. Show me you want me.” Blair and Marcus kiss, and for this moment at least, Blair’s two sides are reconciled.

In the next episode, however, Blair receives proof that Marcus and Catherine are sleeping together. She’s distraught, of course—think of it, this is her second serious relationship in which her boyfriend has cheated on her. Her dress calls back to the beginning of their relationship—a green, purple, and yellow floral dress, much like her brightly colored florals in the Hamptons.

While Blair boots Marcus and Catherine back to England, Serena inadvertently ascends to queen of Constance and walks in Eleanor’s runway show—as Blair said in 1.4, she can’t help but “take” things from her friend. Their rivalry travels with them to New Haven, where they both tour Yale’s campus (2.6).

The morning of the visit, Blair has another Audrey dream—this time, My Fair Lady. Blair imagines herself as pre-transformation Eliza Doolittle, shabby in her dark layers; Serena as post-transformation Eliza, resplendent in the navy-and-white gown and hat from the movie’s horse race scene. The dean plays Henry Higgins—much more enchanted by Serena’s Eliza.

Their color palette carries over to the visit itself: Serena is light and appealing in a white-and-purple striped blazer and white blouse, while Blair is gloomy and severe in a yellow blouse and olive knit tie, cardigan, and skirt. Her interview with the dean follows Serena’s, and when he brings up Serena’s fashion show anecdote, Blair can’t help but let loose:

I know I must seem rather traditional. . . . Well, I’m aware I lack some people’s easy grace with strangers and I don’t exactly make you feel like you’ve know me forever even though we’ve just met. When I laugh, you might not smile just at the coquettish sound of it and I may not be spontaneous or delightful or full of surprises and my hair may not sparkle when it catches the light! Everything worth knowing about me is in that folder. I made sure of it.

What she lacks in charisma or spontaneity, Blair makes up for in control and perfection. Blair believes that if she does things the “traditional” way—wears a prim outfit, takes great care with her application—she will succeed. Both Serena and Blair are invited to dinner at the dean’s house—Blair conning her invitation—and the evening quickly descends into a nasty showdown.

They make up the next morning, both having gone to the dean to plead the other’s case. Serena is still the dean’s favorite for early admission, and Blair’s outfit reflects that. It’s a chaotic mix of colors and patterns: plaid skirt, zigzag blouse, color-blocked cloche, black scarf. This is not the coordinated, perfect Blair that we’ve come to expect; she looks lost, confused, all her planning for nothing.

For the next couple episodes, Blair and Chuck go back to their games. After Blair won’t say “I love you” to Chuck, he tells her to chase him—and she does, in outfits that play with the two sides of her being: on the surface, she’s studious in a white plaid shirt, blue tie, and blue-and-black houndstooth skirt; she unbuttons the skirt to reveal white lace-trimmed stockings.

Still, neither Chuck nor Blair can bring themselves to say those three words: “I think we both know the moment we [say “I love you”] it won’t be the start of something, it will be the end,” says Chuck (2.8). “What we like is [the game].” Much like Blair can’t reconcile her “light” and “dark” sides, Chuck and Blair can’t quite understand how to merge their sexual games with the outward presentation of a “normal” relationship: “Chuck and Blair at the movies, Chuck and Blair holding hands.”

It’s only when Chuck spirals after his father’s death that Blair says, “I love you”—returned, by Chuck, with “Well, that’s too bad” (2.13).

Blair wants to start a new life post–high school, without Chuck. She’s received an invitation to the exclusive Colony Club, and for her tea with the members, she chooses a black dress with a silver diamanté neckline and black beret—what Blair, I imagine, thinks is the mature equivalent of a headband. Serena tries to shame Blair into leaving her tea to help Chuck, who’s crashing and burning at the Victrola. “I’m not abandoning Chuck,” Blair replies. “I’m just saving myself.”

In her Audrey dress, Blair looks out of place among the Colony Club members—country club preppy in pastels, argyle, and pearls. They are also incredibly catty, judging Serena and her outfits, the Basses and their new money. “I thought I was leaving high school behind,” Blair says. “I guess you never do.” And with that, she leaves to rescue Chuck, thus enforcing a false dichotomy: the Colony Club or Chuck, “good” or “bad.” Blair could create a new life for herself and not need some society matrons to do so, and yet the show brings her back to Chuck, again and again, to be emotionally pummeled.

In episode sixteen, Blair is wait-listed at Yale, receiving a spot only after Serena declines her admission. Blair wears very little of Yale’s school color, blue, in this episode, save for touches on her school uniform. In fact, to the opera, she wears a tiered dress in orange—the opposite of blue on the color wheel. To protect her perfect grades for Yale, she’s hazed a new teacher who gave her a B—inviting Miss Carr to dinner and the opera, then abandoning her at the restaurant. Though Blair apologizes for lashing out, Miss Carr informs the headmistress.

Blair attends tea with the headmistress, anticipating congratulations on Yale, only to learn that her admission has been put on probation until she completes detention. Her outfit, much like her chaotic look on Yale’s campus, reflects her emotional state, her expectation to attend Yale in the fall clashing with her reality: her coat, blouse, and skirt in three different autumnal plaids.

Blair loses her spot at Yale in episode eighteen; it goes to her academic rival, Nelly, after the college is told that Blair hazed a teacher. Blair just happens to be playing Countess Olenska in the school’s production of The Age of Innocence, and her fall from grace gives her insight into her character, a “ruined woman with no prospects.”

Her Countess Olenska costume doesn’t look like Michelle Pfeifer’s costumes in the film version. Rather, her costume is yet another variation on her Audrey cosplay: a high-necked black lace gown with a silver brooch. It’s an appropriately mournful outfit, the dress and jewelry evoking the widow’s weeds and mourning brooches of the Gilded Age.

Blair spends the next episode burning her life down, while Serena and Chuck try to douse the flames. At a van der Bilt party, she attempts to seduce Chuck: “Do you remember the first time you saw the real me?” she asks him. “The night Blair danced for you at Victrola. The Blair with none of the hang-ups, none of the frustrations. That’s the Blair right here.” The “bad,” “dark” Blair, I should add.

Chuck turns her down—“It’s not the Blair I want”—and yet again, Blair is told she cannot possibly contain two sides, that she must be one or the other. And yet, her party outfit reflects both: a blue-and-white bandage dress, cream cardigan, and pearl nautical necklace. The bandage dress is unexpected, more body conscious than her usual A-line silhouettes. The color palette and necklace, however, are “good,” “light” Blair, the Blair who once thought she was going to marry Nate. Blues and nautical motifs are classic Archibald, and so it’s no surprise when Nate is the only person who can bring back that side of her.

He reminds Blair that she watches the same Audrey movies over and over because she “likes knowing how things are going to turn out.” While Chuck may want this side of Blair, Nate is the one who understands how to coax it out, why she needs control and reassurance; after a year of uncertainty, he makes her feel secure.

Nate and Blair get back together in the next episode, Blair in more blue. Even so, she can’t quite let go of her schemes or Chuck, and Blair and Nate break up at prom (2.24). By the time graduation has rolled around, Blair has secured a spot at NYU with the help of her stepfather, Cyrus Rose. Chuck, however, still hasn’t told Blair he loves her—though he’s admitted it to Serena and Nate.

At the graduation party (2.25), Blair decides to go bold: a silver-and-black dress with a black embellished headband and silver floral necklace. Gossip Girl called her a “weakling” in her graduation post, but Blair won’t accept the label: “I won’t let [Gossip Girl] be right about me. I won’t be weak anymore.”

She pulls Chuck aside for perhaps the cringiest scene in the series: as she undresses, she asks him what he thinks of each piece, hoping that when she asks what he thinks of her, he’ll finally reply, “I love you.” The look shares the same elements as her Audrey cosplay—black dress and silver embellishments—but shaken up. She’s stripping away all her usual costumery, vulnerable in her simple black bustier. Even her necklace looks like a cockeyed version of the one Chuck gave her in season one.

Chuck can compliment her headband and her dress, but he still can’t say those three words. Blair is left to give this advice to Jenny, her pick for the next queen of Constance: “You need to be cold to be queen. . . . You can’t make people love you, but you can make them fear you.” All at once, her outfit becomes a symbol of her connection with Jenny, also in a black dress.

Chuck finally says “I love you” in the last scene of the finale. He’s gone to France for Blair’s favorite macarons, to Germany for her favorite stockings (you can order online, Chuck!). While Chuck is dressed in a surprisingly simple and muted look, Blair’s is vibrant: a kelly-green coat layered over a yellow embellished cardigan and gold blouse, her headband a gold knot. The green feels springlike and fresh, the color of renewal, but the gold and yellow—usually the colors Serena wears when she’s most “desirable”—are somewhat ominous. Blair and Chuck may be going into the next season in love, but their relationship will soon be tested by their sexual games.

Season Three

Blair leaves her maximalist uniforms behind in season three, favoring, to quote Daman, “very sleek, very minimal, linear clothing that’s almost architectural in design” (“Gossip Girl Style with Eric Daman”). “Architectural,” I think, is particularly telling, considering the role a building will play later in the season. After all, Blair is the new girlfriend of a burgeoning real estate mogul, her color palette “morph[ing]” (“Style”) with Chuck’s.

Though she may be in a happy relationship, Blair is lost at NYU, her designer outfits unappreciated by her more activist- or literary-minded peers—represented by Vanessa Abrams and her old classmate Dan. On her first day (3.2), Blair wears a power-red peplum dress, her accessories a white python headband and gobs of pearls, practically screaming “MONEY.” Blair expects to become queen of NYU easily, so she’s surprised to find that her classmates want pizza and documentaries over her sushi and sake party.

For her party, she changes into the school color, a “royal . . . majestic purple” dress and headband. But, as Daman points out, the “lines here are very severe and again very minimalist and architectural . . . anti-NYU” (“Style”).

Not only that, but Blair’s enemy, Georgina, is her roommate and already much more popular than Blair. Georgina throws a rooftop party, and Blair asks Dan to be her date, hoping to absorb some of his newfound cool. She goes about as casual as Blair gets for the party, and in Humphrey neutrals, too: yellow tailored shorts and a brown printed blouse. Even her beaded necklace is brown, almost the opposite of the luxe pearls she was wearing earlier, so NYU that a fellow student compliments it. Dan tosses aside her yellow headband before they enter the party: “No headbands in college,” he says.

And indeed, even as Blair starts collecting some off-brand minions at NYU (dressing them in knockoffs of looks she wore earlier in the season), she rarely returns to headbands, never wielding quite the control she had at Constance.

Even her dreams have turned against her: In episode six, Blair imagines she’s Bette Davis in All About Eve, watching her rival, Vanessa as Eve, receive an award. Blair awakes in distress, telling Chuck, “I’m Audrey Hepburn! Not some plain Baby Jane.” Blair thinks of herself as the youthful, thin, vivacious Audrey—Holly Golightly or Princess Ann, not Bette as Margo Channing, a middle-aged actress bested by her younger competition. The dream’s looks are closely inspired by the movie’s outfits: Blair in a black off-the-shoulder gown with a brooch, Vanessa in a white gown with beaded cap sleeves. For Blair, black dresses symbolize Audrey, and so it must be especially distressing to wear one as Bette.

The dream is prompted by NYU’s freshman toast: Vanessa is Blair’s biggest rival for the honor. When asked, by Vanessa, why she deserves to deliver the toast, Blair descends into a racist rant in which she compares herself to Marie Antoinette. Blair is used to being queen, and not only that, to being served by minions, many of whom are women of color.

Jenny is now reigning as Constance’s queen, and Blair can’t help but grab at a little of her old power. She even offers to be Jenny’s cotillion mentor (3.9), all while wearing a thin black headband. In fact, I only noticed the headband, which almost blends into Blair’s brown hair, when Jenny called it out: “Your era’s over,” she tells Blair, “and so is that headband.” Jenny doesn’t wear headbands as queen, making the accessory as dated as Blair’s reign; she doesn’t attempt one again until season four.

As this season continues, Blair’s story lines become more and more centered in Chuck’s. He’s just met his mother, a woman he long thought to be dead, and Blair encourages him to open his heart to her. When a scandal forces Chuck to sign his new hotel, the Empire, over to his mother, he realizes she’s secretly allied with his smarmy uncle, Jack Bass.

Bubble Episode

At the beginning of episode seventeen, “Inglorious Bassterds,” Blair confides in Serena over shopping at Matthew Williamson, her outfit a black-and-gold belted dress, black lace tights, and a red Chanel bag. The black dress is very Blair, and yet the gold touches hint at what’s to come. Blair is worried that the betrayal will set Chuck back: “The hotel is proof that Bart was wrong about Chuck. It’s become who he is.”

Serena grabs a dress from the rack and presents it to Blair. “Once Chuck sees you in it, he’ll realize Empire or no Empire, Blair Waldorf loves him and no one else can say that.” Serena leaves to prepare for Nate’s birthday party, and Blair is left holding the dress, admiring herself with it in a mirror.

Suddenly, Jack appears: “She’s right,” he says. “It is a remarkable dress.” Chuck met with Jack that morning, and Jack offered his nephew an indecent proposal: he can have his Empire back, and “all it would cost is [Blair] spending the night with [Jack].”

Jack says Chuck shot down the idea, and so does Blair. When Jack tries to stroke her hair, she slaps his hand away; her gaze goes to the dress, now hung back on the rack. “You should at least try it on,” Jack tells her.

The dress, unsurprisingly, is Matthew Williamson. (The store, weirdly enough, did a window display tie-in for the episode that “feature[d] a brunette mannequin sporting the very same dress alongside window signage that read ‘What Did Chuck Do?’ and ‘Tune In’” (British Vogue).)

Daman chose the dress, a cream halter-neck with gold-and-turquoise beading across the bodice, because he “wanted it to represent innocence, purity, vulnerability—characteristics that are not usually explored with Blair’s character. . . . So the creamy draped chiffon was . . . [the] perfect incarnation to give a nod to Blair à la Joan of Arc or Fay Wray” (British Vogue).

Yes, Blair rarely wears white or cream gowns—as we’ve seen, over and over, she loves black for formal occasions, outfits built up like armor. In fact, the beading on this dress almost looks like a breastplate, perhaps one a high-fashion Joan of Arc would wear. And yet, I can’t help but come back to the gold and turquoise. As I’ve mentioned, gold is not Blair’s color but Serena’s. Blair also never wears turquoise; that’s Lily’s signature stone. Serena and Lily are frequently shamed, sometimes even by Blair, for their sexual histories, for their longer lists of partners; they were even both assaulted by Bass men—Chuck and Jack, respectively—who saw them as women of “reputation.” Perhaps this dress is meant to represent innocence or purity to the viewer, but I don’t think it does to Blair. I think it represents dirtiness and shame, her eye going to it as soon as Jack touches her.

Later that day, Jack sends a box to the Waldorf penthouse, accompanied by a note: “One last chance to save your man.” Even the card is gold. Soon after, Chuck tells Blair that Jack is going to close the hotel, that there is “no way” to save it. “I am everything my father said I was.” Believing she is the only person who can stop Jack from closing the Empire and Chuck from becoming his old self, Blair opens the box; inside is the dress.

Blair arrives at Jack’s Empire suite and quickly strips off her coat to reveal the gown, paired with a gold clutch. Always prepared, she’s had a contract drawn up; they sign it with a gold pen. Blair tries to undo the neck of the dress, but Jack stops her, kisses her.

A kiss is all he wants; “I prefer the woman to want to have sex with me,” he says. Jack seems to understand what Chuck doesn’t: manipulating Blair into trading sex for a hotel is rape. “Chuck chose to give me you [over the Empire],” Jack continues. “He told me exactly which buttons to push. . . . Who do you think sent me to [Matthew Williamson]?” Turns out, Chuck’s money paid for Blair’s dress.

Blair returns to the penthouse, where Chuck is waiting. She’s tied her coat, trying to hide every bit of the dress and her shame. Still, a piece of the beaded bodice peeks through at the collar. In the coat’s black mutton sleeves, Blair looks almost like a scorned Wharton character, her Countess Olenska, the gold like a cameo at her neck. She’s mourning her relationship, her now-broken trust in Chuck. He believes she slept with Jack and places equal blame on her: “You went up there on your own.” She slaps him and goes up to her bedroom.

At her vanity, she stares at her tearstained face, then pulls off the dress and climbs onto her bed. Underneath the dress, she is wearing a strapless romper, the bustier cream, like the dress, but the bottom ruffled black shorts. At her heart, she is light, “pure,” the “good” Blair, but below, she feels “dark” and dirty, shamed into thinking the setup was as much her fault as Chuck’s.

In the next episode, Blair briefly reunites with Chuck, unhappily wondering, “Who else could love me after what I’ve become?” They attend Dorota’s wedding together, he in a light gray suit, white shirt, and beige tie, and she in a beige-and-rose-gold dress, a variation on the gold from the previous episode. Before the ceremony, Chuck gifts her a rose-gold necklace, similar in style to her birthday present but this time smaller, unwanted. He’s happy to have Blair back, but Blair can barely contain her disgust: “We do belong together,” she tells him. “We’re both sick and twisted. If you think about it, we’re incredibly fortunate to have even found each other.”

Chuck and Blair are supposed to be the “happy couple,” the pair that escorts Dorota and her soon-to-be husband, Vanya. Worried that she and Chuck will bring the newlyweds bad luck, Blair confesses their unhappiness to the whole wedding party.

Dorota, ever Blair’s surrogate mother, says, “I wish you to be like me one day, to find right love, good love.” Blair agrees and tells Chuck that she wants “real love. Pure and simple love.” She’d rather be “bored than ashamed.” Once again, Blair has decided that she needs to choose between her “light” and “dark” sides, rather than find a balance between both.

In episode twenty, Blair visits Nate at Columbia and runs into some familiar faces: two Columbia freshmen who attended Eleanor’s fashion show in episode sixteen. Unlike her NYU classmates, the Columbia students are obsessed with Gossip Girl; they even wear headbands (though Blair corrects: “The bow goes on the right”).

Still miserable at NYU, Blair pretends she’s transferring to Columbia. She even wears a coat in one of Columbia’s colors, light blue, with a bright blue hat and bag. But still, no headband. Blair isn’t yet queen of Columbia, though she discovers, at the end of the episode, that Chuck secretly submitted her transfer application—she’s in.

A scheme brings Chuck and Blair in close proximity in episode twenty-one, but Blair isn’t sure if they should get back together. “If I got through my fear for you,” Chuck says, “you can for me.” (Uh, saying “I love you” when you’re scared isn’t the same as getting back with someone who treated you as property.) Chuck sets a ticking clock: Blair must meet him on the observation deck of the Empire State Building the next day or he’ll be lost to her forever.

Blair can’t decide whether to meet Chuck, but she takes her frequent sightings of the Empire State Building as signs that she should. (I would argue that’s just the nature of a very tall building.) Both her outfits in the episode call back to the two previous finales, to getting and losing Chuck. When she finds Chuck at the Empire, she wears a green cape over a black floral dress and a black-and-white polka dot scarf, the cape and yellow bag reminiscent of the bright green and yellow she wore when Chuck finally said “I love you.” They briefly reunite, only for Blair to learn that Chuck had questionably consensual sex with Jenny after he decided Blair wasn’t coming. Much like Chuck blamed Blair for the hotel trade, Blair directs most of her fury at Jenny, banishing her from the city.

Blair invites Serena to spend the summer in Paris. This time, she’s dressed in a nautical-inspired outfit, not unlike the one she wore in the season one finale, when Chuck abandoned her. The straw hat and navy-and-white cape remind us of her season one straw hat and sailor dress, while underneath are a boat-printed blouse and red pencil skirt. Blair is hoping to forget about Chuck and find new love in Paris, but even in her wardrobe, there’s always a little something to remind her of his betrayal.

Season Four

In Paris, Blair moves from the sleek, architectural dresses of season three to frilly, romantic confections. Her love life, however, is at a standstill. She’s been spending time at museums, looking at her favorite artworks and hoping to find someone who’s feeling the same things she’s feeling.

That is, until Louis: he approaches her at the Louvre (4.1), as she stands in front of her favorite painting, Édouard Manet’s The Luncheon on the Grass. Perhaps it’s the duality of the subjects that so appeals to the divided Blair: the nude female figures contrasting with the clothed male figures. Her dress is a cream-and-orange abstract floral, almost an Impressionist painting itself. She pairs it with a pearl choker and a brown leather watch—set to EST, which is how Louis knows she is an American.

Based on a passing reference, Blair believes Louis must be a prince of Monaco. But on a double date with Serena, Louis reveals that Serena’s date, Jean Michel, is royalty and Louis is his driver. This, of course, doesn’t go over well with Blair and her princess fantasies. She even wore her Audrey cosplay: a black dress with rhinestone embellishments and a silver necklace.

Just as Marcus pretended to be a commoner, Louis is only pretending to be a driver, testing Blair to see if she is genuinely interested in him, not his princedom. Though she fails the test, he gives her a second chance in episode two.

Chuck has also landed in Paris. He’s now dating a Frenchwoman, Eva, and living as the poor “Henry Prince.” Serena believes that only Blair can convince him to return to his life in Manhattan, but Blair isn’t interested. “I’d forgotten what it was like to just have fun with a guy,” she tells her friend. “I’ve been waiting all summer to feel sparkly again.”

Louis invites Blair to a Givenchy ball (Givenchy, fittingly, designed many of Audrey’s on-screen looks, including her iconic black dress). He sends over a rack of gowns, even directs her to Harry Winston to pick out a bit of sparkle. At Harry Winston, Blair runs into Serena and a French inspector, who tell her that Chuck was shot earlier that summer trying to protect the Winston engagement ring he bought for Blair. She’s finally convinced to stop Chuck and dashes to him in her red strapless ball gown and pink diamond necklace.

Though Blair, too, must return to New York, she gives Louis a glass slipper: one of her buckled Roger Viviers (not unlike Carrie’s Manolos in the Sex and the City movie, as I discussed in this post). Back in the city, Blair’s starting her first year at Columbia as a member of the exclusive Hamilton House, her membership bestowed with a silver Tiffany key necklace (4.3).

Interestingly enough, Blair regularly wore a very similar silver key necklace at the beginning of season three. Perhaps this new key is meant to call back to that period, when Blair was happy with Chuck and unhappy at NYU, or simply to show that Blair and her Tiffany tastes fit perfectly at Columbia, where she quickly acquires a new roster of minions. As queen again, Blair regresses to a less sleek and mature style—lots of brightly colored and patterned flippy skirts and tops, her minions in a similar bright palette.

After Blair sabotages Chuck’s relationship with Eva, she and Chuck go to war (4.5). By episode seven, they agree to a truce and hammer out a treaty with the help of Serena and Nate. Blair dons a headband for the first time this season: solid blue with a green tweed skirt suit. The suit is typical serious, planful Blair, but the headband picks up Chuck’s blue palette, perhaps signaling the connection they still share, even as they divvy up the city.

Peace soon turns to hate sex, which then turns to genuine feelings. In episode nine, Blair meets with Nate’s mother, Anne, who wants her to become the new face of Girls Inc.—without Chuck by her side. “People may forgive the choices you’ve made in your past,” says Anne, “but if you want this foundation in your future, I’ll need some assurance that Charles won’t be a part of it.” Concurrently, the Empire’s publicist tells Chuck that he needs to embrace his hedonist image—and not a steady relationship with Blair—if he wants his hotel to bounce back.

Chuck throws a Saints and Sinners party, Blair attending as a sinner in a black mask and red slip trimmed with black lace; after all, lingerie almost always signals her “dark” side. There, Blair and Chuck are caught kissing, and Anne rescinds her offer, more of a “saint” in a buttoned-up trench and pearls. “The man you’re with may not be a reflection of you,” Anne says, “but you will always be a reflection of him.”

The Empire’s publicist loves the kiss; she says the romantic gesture was the “perfect balance” to Chuck’s hedonism. She’s even already thinking about photo ops for Blair: “Chuck Bass’s girlfriend at store openings, fashion shows, that kind of thing.”

As a man, Chuck doesn’t have to choose between being “good” and “bad,” saint and sinner, but as a woman, Blair does. She ends their fling: “I have to be Blair Waldorf before I can be Chuck Bass’s girlfriend,” she tells Chuck.

Thus begins Blair’s quest to become a “powerful woman” independent of Chuck. As she does, she also becomes close to Dan, both having realized that they share the same love for museums and art-house films. Their color palette and patterns start to merge—lots of black, white, gray, and red plaid. Dan even sparks the idea for Blair’s career path after she rejects an internship with Waldorf Designs (4.12). He tells Blair: “You care about fashion more than most people care about anything. You used to send girls home crying for wearing tights as pants. . . . You’re an evil dictator of taste, Blair. Why deny it just because it’s what your mother does?”

Through dogged persistence, Blair secures an internship at W magazine, her first step toward becoming an “evil dictator of taste”: an editor of a high-fashion magazine. She keeps her black, white, and gray color palette, incorporating touches of luxe metallics and sophisticated textures, strong-shouldered blazers and sheath dresses, even pants.

Many of Blair’s ideas about fashion come from Audrey movies, and I imagine she was inspired by the Diana Vreeland–esque editor in Funny Face, who proclaims that readers should “Think pink!” even as she sticks to her plain gray skirt suit. By episode fourteen, Blair accepts an assistant’s job at W, despite her full course load.

In episode fifteen, Blair attends Chuck’s Valentine’s Day party, hoping to procure an interview with Raina Thorpe for W. Raina is Chuck’s new girlfriend, the daughter of his real estate rival, Russell Thorpe, and a true “powerful woman” herself. Blair believes Chuck is only pretending to like Raina to take down Russell, but at the party, she and Dan overhear Raina breaking up with Chuck and know his feelings are true. Both Raina and Blair are wearing champagne dresses; while Raina’s is fully beaded, Blair’s metallic roses wear away at the bottom. Raina is Chuck’s focal point, and Blair is fading away.

When she can no longer balance her schoolwork and job, Blair is fired from W. She’s so exhausted she wears mismatched shoes (4.16), one of which is the sister to the buckled heel she gave Louis. It’s our first hint that Louis will return soon, glass slipper in hand. Before then, Blair and Dan must decide if they have feelings for each other. They’ve been hiding their friendship, sneaking to museums and movie theaters together, and both wonder if they’re suppressing something more.

They agree to one kiss (4.17), Blair in a black-and-pink floral dress and pearl pendant necklace—much like the romantic floral dress and pearl choker she wore the first time she met Louis at the Louvre. It’s another hint that Louis is returning, but perhaps also a sign that Dan is that person she was looking for in Paris, the kind of person who feels the same things she’s feeling when she looks at paintings.

For Dan, the kiss affirms his feelings for Blair, while for Blair, it confirms that she wants to be with Chuck now. She even plans to tell him in episode eighteen, after a shoot for the Modern Royalty photo book. Chuck is being photographed solo, and he can’t help but play a jealous trick on Dan. When Blair learns what Chuck has done, she realizes that he’s not ready for a serious relationship.

Chuck was hoping to be photographed with Blair; he even bought her a black strapless gown to match his black suit and shirt. Blair notes that the gown looks like “the one Diana wore after becoming a princess,” and Chuck confirms it is. Based on the dress shown, I think it’s actually meant to be a gown Diana wore before she married Prince Charles, just after they became engaged. (She was nicknamed “Daring Di” for the low-cut neckline.)

No matter which era it’s from, the dress begs the question: Does Chuck know anything about Princess Diana’s marriage? Yes, there are the parallels between Blair and Diana—their complicated relationships with their mothers, their eating disorders, their skilled employment of fashion—but the princess spent years in an unhappy marriage and then died in a car crash! Quick, someone play Chuck season four of The Crown.

At the end of the episode, Louis arrives in the city with the Vivier heel, and Blair begins dressing even more like she did in Paris: ruffled, romantic, floral, with a bit of sparkle. She and Louis quickly become serious, and she tells him all about her past. Louis’s family wants him to marry, though his mother disapproves of a bride whose entire life is on Gossip Girl. Now that Blair has won over Louis, she must win over the court, too.

Louis gives her a blush beaded dress for the occasion, perfectly in line with her more romantic, sparkly wardrobe, the “joy” that her relationship with Louis brings her. She’s charming and composed until Chuck arrives and humiliates her in front of the court. Despite the scene, Louis still wants to marry Blair and proposes that evening; when she goes to tell Chuck, he punches a window and a shard cuts Blair’s cheek.

Ashamed, much like she was after the hotel setup, Blair tells Louis that her new engagement ring cut her face. When he discovers the real cause, he implores her to be open with him: “The only way [this marriage] will work is if you show me all the parts of yourself, even the ones you’re ashamed of.”

For the umpteenth time, Blair must reconcile her two sides: As she tells her stepfather, Cyrus: “It’s not all light and bright in here. There are some places devoid of even a hint of sparkle. . . . Chuck was the only one who ever loved [my dark side]. But he couldn’t see the rest. What kind of princess schemes and plays sex games and dreams herself into Hollywood movies?”

Blair’s engagement dress shows these two sides that she tells Cyrus about: her sparkly, light side, and her dark, depraved side. The top half is sparkly and frilly, silver embroidery and pink fabric flowers, evoking the blush gown that she wore to charm the court; the bottom half is simple, unembellished black, calling back to the Diana dress. Honestly, the whole thing is very Freudian: the light side is close to her head, her mind, while the dark side is her body, her sexuality.

After Chuck rescues her from Russell Thorpe, Blair and Chuck sleep together. She plans to break her engagement to Louis, but Chuck stops her, believing she will be happier with her prince. In this scene, a pink embellished coat covers most of the dress, “light” winning over “dark.”

Season Five

Newly engaged to a prince, Blair’s wardrobe inspiration shifts from Hollywood royalty (Audrey Hepburn) to real-life royalty (Princess Grace, Duchess Kate). Her headbands are replaced by “Kate Middleton–esque fascinators and hats” (“5 Years of Iconic Style”) and her more elaborate outfits by simpler printed day dresses or skirts and blouses, often paired with statement necklaces. In episode three, Blair even walks in a Jenny Packham fashion show; Packham is one of Kate’s go-to designers.

Most importantly, Blair wears a lot of blue, much like Kate. For Kate, blue is meant to symbolize Cambridge, to remind us of her sapphire engagement ring; for Blair, the color encompasses her monarchical fantasies: The Marie Antoinette mural in her childhood bedroom is all in blue. She wore blue frequently when she was queen of Constance and dreamed of marrying Nate. And, of course, there’s French blue. How can the color not evoke her engagement to Louis?

There’s just one crimp in the fantasy: Blair is pregnant and (in a callback to season one) she doesn’t know who the father is: Chuck or Louis. She hasn’t told Louis, and so she hides her morning sickness from him and his visiting sister, Princess Beatrice (5.2). Once Beatrice learns of Blair’s teenage bulimia, she believes that Blair’s constant nausea and bathroom breaks are the return of her eating disorder. Naturally, this is also the episode when Blair learns how constricted her fashion will be as a princess:

Blair: [I’ll wear] Wu for my welcome parade, short but regal, and Alaïa would put Charlene and her swimmer’s body to shame at Albert’s ball.

Beatrice: Those will never do.

Blair: Why? They only use children to sew the beading.

Beatrice: You cannot have bare shoulders, exposed knees, anything formfitting. Too much skin borders on Bruni.

Blair’s fantasy of outshining other women’s bodies with her own not only ties back to her eating disorder but also to her pregnancy. Her body is going to change as her pregnancy progresses, and while that doesn’t mean she can’t wear what she wants, Blair still seems to be imagining her thin, unpregnant self as princess.

With encouragement from Dan, Blair obtains a paternity test: Louis is the father (5.3). And yet, their happiness is haunted by Louis’s jealousy. He doesn’t trust Blair with Chuck or Dan, who recently published a novel in which “Clair Carlyle” is the star and love interest of “Dylan Hunter” (5.4).

Even Blair isn’t sure she can trust Chuck. He’s started going to therapy, participating in philanthropy; after years of whiplash between “good” and “bad” Chuck, she doesn’t know which one to believe. Her worries manifest in an Audrey movie dream, this time Sabrina (5.7). Blair imagines herself as Sabrina in a white-and-black dress inspired by Audrey’s Givenchy gown, Chuck as Humphrey Bogart in a white dinner jacket. He offers to help her down from a ladder. “How do I know I can trust you?” she asks and falls just as she wakes up.

In real life, Blair has traded her more formfitting day dresses for tentlike counterparts—perhaps to comply with the monarchy’s strict dress code, perhaps to disguise her growing pregnancy from the public eye. Still, I wonder if Blair has trouble dressing her changing body, favoring loose silhouettes to hide the foreign shape underneath. As her relationship with Louis continues to deteriorate, she also stops wearing fascinators, her princess fantasy turning to nightmare.

In episode nine, Blair insists on attending one of Chuck’s therapy sessions. She wants to know how Chuck became “good,” believing that she is the one who turned Louis “bad.” “All this time,” she tells Chuck, “I’ve blamed you for pulling me into the dark. It was me who brought out your dark side. And now that I’m with Louis, I’ve done the same to him.”

Chuck disagrees: “You never pulled me to the dark side, Blair. You were the lightest thing that ever came into my life.” While their conversation is sweet, it only serves to enforce the dichotomy in Blair’s mind: she is half-light and half-dark, rather than a whole, rounded being, full of all the kinds of contractions that make her human. 

With Dan’s help (5.10), Blair and Chuck run away, planning to raise Blair’s child together. On their way to the airport, their car crashes. Blair miscarries, and Chuck loses a lot of blood. Devastated, Blair begs God to save Chuck’s life, promising to marry Louis. When Chuck awakes almost immediately, Blair takes his recovery as a sign her prayer worked.

Blair tells only Dan about her promise to God, and they secretly attend church together as Blair tries to understand if she should keep her pledge (5.11). As she avoids Chuck, her wardrobe turns to Dan: a red plaid jacket, white vest, and black skirt—the color palette evocative of their season four friendship, the plaid and vest both Humphrey staples. Dan even accompanies Blair to her Vera Wang wedding dress fitting, the first of the show’s parallels between Dan and Blair and Dan’s father, Rufus, and his now wife, Lily.

In 5.13, the show’s hundredth episode, Blair and Louis marry. “Who would’ve thought,” Gossip Girl wonders, “that in just five short years, [Blair] could turn that headband into a tiara for real?”

Blair’s wedding dress is simple at first glance, a strapless ball gown with a little tulle bow at the waist. On closer look, the details come out: Daman describes the dress as “old world . . . a layer of lace on top of it . . . tiny little handcrafted buttons that go all the way down the back” (“5 Years”). The rest of the ensemble includes a diamond tiara, a veil, and a diamond necklace that looks like a poor man’s version of Chuck’s birthday present.

Gossip Girl interrupts the ceremony with a blast: a video of Blair proclaiming her love for Chuck before the wedding. Blair and Louis still make their vows, but Louis reveals at the reception that their marriage will be loveless, only for show. Blair escapes with Dan, hoping to get a quickie divorce in the Dominican Republic; Louis’s mother tracks her down first (5.14). The Grimaldis had waived Blair’s dowry, but if she defaults on the marriage now, the Waldorfs will have to sell Eleanor’s company to pay the enormous debt.

Resigned to her fate, Blair embarks on her honeymoon with Louis. She’s changed into her princess uniform, a pale blue dress with a blue fascinator—the color that once symbolized her fantasies now heavy with sadness and disappointment.

Her own romantic dreams dashed, Blair schemes to reunite Serena and Dan—wearing, naturally, a dress with a built-in tweed vest (5.15). Dan, however, wants only Blair; he kisses her again, but this time she feels something. “Dan loves me for me,” she realizes (5.16)—not for only her “light” or “dark” parts but her whole self. Dan has seen the worst of her schemes—he and his sister were the targets of a few—but also her most beautiful, intimate thoughts and dreams. He is motivated by her happiness, even if it means sacrificing his own. When Blair discovers that Dan sent the video of her confession to Gossip Girl, she is quick to forgive him because she knows he cares for her well-being: “I couldn’t stand to see you so unhappy,” he tells her.

Blair secures her divorce in episode nineteen; as she soon learns, Chuck secretly paid her dowry. Though Blair is happy to be free, she mourns the loss of her fantasy: “My whole life I wanted to be a princess,” she tells Dan. “I may have married a prince, but I never got to be a princess.”

Dan wants Blair to have her chance: He brings her to the Met steps in a fluffy pink ball gown and white tweed jacket; he even places a tiara on her head—cubic zirconia, much to her chagrin. There, she is flocked by a group of Constance girls, dressed much like Blair in season one. Though she may no longer be a princess on paper, the girls treat her like one.

Blair continues to favor printed day dresses, often in vibrant, romantic florals, and statement necklaces. In her relationship with Louis, the dresses evoked Duchess Kate, but in her relationship with Dan, they evoke Lily. She even wears them with her hair in a bun, Lily’s signature style. Like Lily and Rufus, Blair and Dan must navigate the union of their two worlds, Upper East Side and Williamsburg. In episode twenty, for example, they decide to throw a salon together, Blair in an appropriately artsy van Gogh–like dress.

Blair, too, must rediscover herself: “Somewhere between being traded for a hotel and selling out for a tiara, I lost my true self,” she says (5.21). Dan, however, says he fell for Blair right in the middle of that time line, when they interned at W: “That girl is fiercely strong, independent, outspoken, beautiful, capable of anything, and no man or magazine should be able to take that away from her.”

And yet, Blair is quickly swept back into Chuck’s schemes. Dan wants her to accompany him to a writer’s retreat in Italy, but she misses their interview, sending Serena in her place (5.23). Serena still harbors feelings for Dan and pretends to be Blair in a blue-and-yellow floral day dress, yellow coat, and chunky necklaces. She even throws on a blue headband, though Blair hasn’t worn one in a season. Considering how much Blair has been dressing like Lily, you have to wonder if Serena pulled the pieces from Lily’s closet, the color choices inspired by Blair’s van Gogh dress.

Both Blair’s friendship with Serena and her relationship with Dan implode when Gossip Girl begins blasting scans from Blair’s diaries (which are, I should note, all Tiffany blue). As Blair tells her mother, she doesn’t know which love to choose: Dan, who makes her feel “strong and safe,” or Chuck, who makes her feel “vulnerable . . . devastated . . . [and] happier than [she’s] ever been.” Instead of pointing out that a relationship filled with euphoric highs and shattering lows is probably abusive, Eleanor offers her daughter Waldorf Designs upon her imminent retirement. Blair, despite having rejected such a career path in season four, accepts.

She chooses Chuck, but he rejects her. He’s just been ousted at Bass Industries, thanks to his recently resurrected father, and has no interest in being “Mr. Blair Waldorf.” “The only reason Waldorf Designs has a future is because I gave mine up for it,” Chuck says. “I always put you first and you bet against me every time.” Okay, bud!

And so, Blair travels to Paris with Eleanor, back in a big, silly blue bow to “reign over a new kingdom.” Chuck and his uncle Jack head to a Monaco casino, the first step in their plan to win back Bass Industries. During the game, Blair unexpectedly arrives. “You fought for me all year,” she tells Chuck, Leighton Meester delivering the lines like she’s about to be executed. “I’ve come to fight for you. You’ve always said I bet against you. But this time, I’m all in.”

Blair’s gown reminds me of the Matthew Williamson dress from season three: though the color is orange, not cream, the neckline and swirled gold beading are similar. She even has a turquoise cuff on one wrist. Blair rarely wears this kind of neckline, or gold beading or turquoise for that matter, so the parallels feel intentional, especially considering that Jack told Blair that they were at the casino. Once again, Blair is called upon to win back Chuck’s property, even if it means sacrificing herself.

Season Six

Blair and Chuck separate to accomplish their goals: Blair, successfully taking over Waldorf Designs, and Chuck, defeating his father. Blair wears the Harry Winston engagement ring on a chain around her neck; when Chuck conquers his “bad dad” (to quote Dorota), he’ll put it on her finger.

Like many fashion designers, Blair settles into a uniform: a two-piece set, consisting of a peplum-waist top and a knee-length A-line skirt. In episode three, when she stages her debut runway show, her two-piece set is in power red, her headband in the same shade. 

The show seems to think it’s bringing back a nostalgic Blair—all the headbands and disordered eating and snide, sometimes racist comments of seasons one and two—but in reality, Blair just seems lost and frenzied. She hasn’t been eating or sleeping while she prepares for the show, and it’s unclear if she even wants to be a successful designer, or if she just wants to win Chuck and impress her mother. “This business is my family,” she yells at Dorota. “It is the family jewel. It is what Chuck paid my dowry to save! If I’m not successful at this, we might not even end up together!”

Chuck, meanwhile, has become the supportive boyfriend that Dan was in season five, setting up the runway while Blair is on bed rest. Dan, therefore, must become Chuck, scheming and skeevy. Dan encourages Blair to go “dirty” for the cotillion dress she’s designing, and so she does: a loose, conservative wrap strips away to reveal a tight gown with a stomach cutout (6.5).

Blair, still enamored with Audrey, wears a black sequined dress, diamond earrings, and pearl headband to cotillion. There, she learns that Dan and Serena slept together when he thought she was back with Chuck. Dan tries to explain how Serena manipulated him, plied him with drinks, but the furious Blair snaps back: “In order to claim date rape, you have to say no.” And as fucked up as that statement is, I think it really summarizes how Blair feels about sex and assault. She thinks because she agreed to sleep with Jack, because she didn’t say no to his proposal, that she has no right to claim the trade as rape. She blames herself equally, when Chuck set her up with an impossible choice.

Though the “dirty” cotillion dress is a huge success, Eleanor is not happy with the direction in which Blair has taken her company and flies back to New York to fix her daughter’s “decorum disaster.” The problem, Eleanor tells Blair (6.6), is “you and your split personality . . . your dark and scheming and frankly sexually inappropriate side. . . . The deviant half has to go.” In this meeting, Blair is without her headband, her power. Again, she’s being told that she must sacrifice her “dark” side for the “light,” her sexual desires confused with her scheming and bullying.

At first, Blair attempts to blackmail her old classmate, Nelly, into writing a positive profile for Women’s Wear Daily. Only through a conversation with Nelly does Blair realize that her dark side is her “talent.” Everyone dressed like her in high school, she says, because they were “fascinated by [her] ferocity” (or, you know, kept hostage by her insecurity). Blair is arriving at the exact same conclusion drawn in season four: she is an evil dictator of taste. This time, however, instead of moving forward, trying to start an independent career in magazines, she moves backward: launching “a line for high school girls inspired by [her] Constance uniform,” B for Waldorf. Though her “bad” side may suddenly be framed as beneficial, it’s still kept separate from her “good.”

For the opening of her Barneys CO-OP pop-up shop (6.7), Blair, again, is in a black dress, silver necklace, and power-red headband. The line itself seems to consist of pinstripe blazers, ties, and vests, and other uniform staples—Serena calls the clothes “beautiful and original” while standing in front of racks of plain black skirts and white blouses, creating an unintentionally hilarious juxtaposition. The imagery promoting the line is especially interesting: a headless shot of a white girl wearing a uniform created from the pieces, “B for Waldorf” and “XO” for “Exclusively Ours” printed across her body. It looks like the cover of a 2010 YA novel.

The line is a great success; its target audience—private school teen girls—love it. One of them is even wearing a mini version of Blair’s two-piece red set as she shops. Unfortunately, Blair’s achievement is dampened by Chuck’s sad dad issues. He’s failed to defeat Bart, and therefore, they can never be together; Blair’s success is not enough for both of them.         

Rather than say, “Get stuffed, you big baby,” Blair encourages Chuck to try again. (For some reason, this involves her wearing a god-awful Pocahontas stripper costume on Thanksgiving (6.8). Again, really leaning into the racism this season!)

After Bart falls off a building in front of Blair and Chuck, they get married to avoid testifying against each other (6.10). For her second wedding, Blair eschews white for a pale blue beaded gown and diamond headband, Chuck in a matching pale-blue-and-white tux.

Five years later, Blair and Chuck have a toddler, Henry, and Blair is still running Waldorf Designs, even adding a capsule collection with her old rival, Jenny. For Serena and Dan’s wedding, Blair chooses a beaded bronze dress, a bow on each strap. Chuck’s boutonniere matches her dress, but there’s no connection between her and Henry, in wardrobe or name or interaction. For in truth, Blair’s arc was all in service of Chuck’s: her success with Waldorf Designs to fulfill her end of the bargain; their child to correct Bart’s wrongs, instead of Eleanor’s.

I do wonder if the show really understood why viewers connected with Blair: Yes, it was fun to watch her dictate school uniforms and toss around catty comments, but it was also refreshing to see a girl who was so outwardly assured and so inwardly insecure, to hope that she would one day find true confidence. Yes, it was fun to see Blair and Chuck play their sexual games, but it was also refreshing to see a girl who so obviously enjoyed sex, to hope that she would one day learn that being sexual does not make her “dark” or “dirty.” In the end, I think, we were given the superficial trappings—a fashion line for high school girls, a marriage to Chuck—without the deep work. Blair is still “good” and “bad,” and never quite do the two meet.

[Next Thursday, 6/10, I’ll reveal what I think these characters would wear now and which teen soap I’ll be covering for volume two.]

DP on GG

My partner, Daniel, spent 2020 overhearing episodes of Gossip Girl from various rooms of our apartment. This is his birthday week (Happy birthday, Daniel!), so let’s honor him with his best rant:

CL: [These characters] have no self-restraint.

DP: Of course they don’t have any self-restraint; they’ve never wanted for anything in their lives. I want these people to have the same experience I had in high school: being super stressed-out and waiting an hour for the Q85 bus and three Q4 buses show up within that hour and you don’t know where the Q4 goes, but it doesn’t go where you need to go.