The Fantasy of Serena van der Woodsen

Originally published on Substack 4/22-4/23/2021

[This profile contains discussion of suicide and sexual assault.]

From the moment she walks through Grand Central Terminal, Serena van der Woodsen becomes a mythic figure: beautiful, charismatic, effortless in her style. She “picks up whatever [clothes] she finds on the floor”—likely designer—and wears “them with her old jeans and her great boots and her slouchy cap” (“Gossip Girl Couture”). Many of her most memorable pieces are in gold or yellow, the color of her voluminous blond hair, the overall effect like “staring into the sun” (“5 Years of Iconic Style”). (Even her bedrooms, in both her family’s and the Waldorfs’ penthouses, are done in gold and yellow.) She just can’t believe she’s the center of attention, all while wearing the most light-catching gold sequined dress. Everything about Serena, from her long waves to her glittering dresses to her dripping chain necklaces, is tactile, sensual—something to touch. For Serena’s costumes and story lines, from the very first episode, when we learn that she slept with her best friend’s boyfriend at the Shepherd wedding, are always imbued with sex and desire.

In past profiles, I’ve talked about the way Gossip Girl costumes quietly reinforce the show’s messaging about sex—the way Jenny Humphrey’s costumes reflect her “purity” or Vanessa Abrams’s Snowflake Ball dress hypersexualizes her body. But until Serena, I hadn’t come across a character whose costumes were overtly discussed, both by the show’s producers and costume designers, in terms of sex. In special extras like “Gossip Girl Couture” and “5 Years of Iconic Style,” grown adults describe Serena’s high school uniform as “a bit sexier, a little more askew” and “a tousled, sexy, just-rolled-out-of-bed look”; her style inspiration as a model off duty like Kate Moss, then in her thirties. That’s not to say that a sixteen-year-old girl can’t want to be sexy and sexual, but rather that Serena’s sexuality is filtered through this adult lens, infusing her messiness, her youthfulness, her carelessness, with a kind of ease and easiness.

During Gossip Girl’s run, media coverage picked up on the sexiness and sexualization of the character and her fashion, even if it was only to poke fun: Vulture’s recaps kept track of Serena’s employment of the “cleavage rhombus.” The red carpet blog Go Fug Yourself bestowed the nickname “Boobs Legsly” on Serena’s actress, Blake Lively, for her legs- and cleavage-baring outfits. And I do think, as the show continued past high school and Lively’s fame grew, the media had difficulty separating the actress from the character, especially as Lively became more hands-on with Serena’s costuming. As head costume designer Eric Daman told Fashionista, “Blake and Serena had a symbiotic relationship, in a way, stylistically. . . . She got more and more involved in that way as Serena grew and as Blake grew.” Serena even received her own Fitzgerald adaptation story line less than a year after Lively auditioned to play Daisy Buchanan in The Great Gatsby.

Still, even as Serena’s arc and style develop, moving from school uniforms and sparkly dresses to workwear, she can never quite find the happy medium between the guilt-ridden girl who ran away from the Shepherd wedding and the idealized object that her first love, Dan Humphrey, created. She can’t help but return, again and again, to Dan, to the fantasy she so wants to be, the validation she craves after years of being told that she is “beautiful” and “sexy” and not much else. For as much as Gossip Girl loves to sexualize Serena, the show would never allow her to remain bad Serena—debauched Serena. No, Serena must become good Serena, golden Serena, controlled Serena—properly married and put into place.

Season One

Serena returns to the city in the pilot, having spent her sophomore year at boarding school in Connecticut. In Grand Central, she is spotted by Dan, a classmate and scholarship student who’s long harbored a crush on her. As discussed in his profile, her outfit mirrors his: both in striped tops and brown jackets, Serena’s a Breton-style navy-and-white shirt and a brown leather jacket, paired with a gray tailored vest, jeans, boots, and brown leather Coach bag. Around her neck, she’s knotted a jaunty gold kerchief. The overall effect is much more restrained and conservative than we’ll ever see again—covered, literally, from neck to toe. She’s about to convince her friends, her family, that she’s looking for a fresh start, to leave behind her years of sex, drugs, and parties.

Serena ran away to boarding school without saying goodbye to her best friend, Blair Waldorf, and Blair is reluctant to resume their friendship, her past year spent soaking up all the attention Serena left behind; Blair is reigning queen of their high school, Constance Billard School for Girls.

The differences between the two girls are obvious from the first instances of their uniforms. Blair is coordinated, rule-following, in a high-neck blouse and crossover tie. Serena leaves her tie undone, her collar unbuttoned and tails untucked; throws a glittery, attention-grabbing trench on top. Her skirt, even, is shorter and a different pattern than the other juniors’. To quote Daman:

[Serena] wears her school’s uniform skirt from her freshman year, so it’s a different plaid than the other girls are wearing. . . . I think it worked really, really well that she didn’t wear collared shirts, and that we saved that for Blair and her cronies. That was the initial thing that set the two looks apart, that we took a little bit of liberty; Serena was such a free spirit that she was like, “I’m just going to wear my Henley and my skinny tie” (Fashionista).

Now, as you might’ve noticed from this first uniform, Serena does occasionally wear a collared blouse to school, almost always when she wants to be seen as serious and mature, as she does in the pilot. Otherwise, Serena usually favors a white Henley or T-shirt with her uniform, no collar to tighten her tie around.

Serena convinces Blair to meet her for a drink and then arrives all in cream and white—blazer, shirt, necklace. Blair herself is dressed in a black turtleneck, their black and white outfits setting up their initial dichotomy on the show: reformed angel and scheming witch, “good” and “bad.” Though Blair is initially resistant, the girls make up. Once Blair leaves, Chuck Bass offers to get Serena something to eat in the kitchen; his father, Bart, owns the building.

In the kitchen, Chuck reveals that he knows what happened at the Shepherd wedding. He tells Serena that she’s “more like [him]” than she wants to admit, forces himself on her; he, too, is dressed in light colors, pastels, and suddenly the color scheme highlights this shared secret, Chuck’s perception of their mutual wickedness. The scene cuts between this attempted assault and Serena and Nate Archibald sleeping together, Serena in a gold tulle dress, as luxe as the Campbell Apartment around them. The comparison is jarring, the dreamy soft focus of the flashback juxtaposed with the harsh light of the present day.

Serena manages to escape Chuck’s grip, and as she runs out of the kitchen, she accidentally bumps into Dan and drops her cell phone. Dan comes back to the hotel the next day to return it and leaves with a date with Serena. In this scene, she’s wearing cream again, this time a dress, and a gray plaid trench—plaid being the Humphrey pattern of choice.

For their date, Serena chooses a gold sequined minidress with black tights and booties, outside paired with a black scarf and denim jacket. She stands on the hotel’s stairway, glittering, the scarf and jacket not yet on; when Dan spots her, he’s mesmerized. Gold symbolizes wealth, success, splendor, and so Serena wears the color (or its lesser cousin, yellow) when she’s at her most desirable, and often, her most unattainable. It’s no wonder that Dan can’t look away, his fantasy staring down from her pedestal.

The next morning (1.2), Serena stops by the Waldorf penthouse, but Blair no longer wants to be friends; Nate told her about the Shepherd wedding. “I always took you for a whore,” she tells Serena. “I never knew you were a liar, too.”

Serena’s mother, Lily, wants her to attend the Bass brunch; Serena agrees to go if she can bring Dan. The “whore” comment still echoing in her mind, Serena yet again chooses white, this time a glittery, flower-embroidered dress, little touches of gold from her coin purse and necklaces. The dress is sweet, almost childish; the flowers unexpected. Serena rarely wears florals, but Blair frequently does, and so the dress feels like a white flag to her best friend. A best friend, I should add, who has no interest in reconciliation. At the brunch, Blair tells Dan about the Shepherd wedding; he leaves, his perfect image of Serena shattered.

Both Serena and Dan, and Serena and Blair, make up by episode four. In episode five, Dan takes Serena on their first real date, complete with a town car and a fancy restaurant and everything Serena finds boring on the Upper East Side.

Not knowing Dan is planning such an elaborate night, she initially dresses in a striped tank, jeans, silver feather earrings, and brown boots and a hobo bag—the stripes a shared pattern between her and Dan since the pilot. When she sees Dan in his suit and tie, she changes into a dressier look—a studded black cocktail dress and sheer tights, keeping the earrings but taking a black quilted purse that her mother insists on. Ultimately, they end up playing pool at a dive bar, the perfect date abandoned for something more suited to both of them.

Their relationship progresses over the next few episodes, Dan accompanying Serena to a masked ball in episode six. Yet again, she is in her power colors, gold and yellow: a yellow gown with a black furry shrug and gold filigree mask.

In episode seven, Dan and Serena almost have sex for the first time. Both are nervous, Dan because he’s never had sex before and Serena because she has and never connected with her partner, always treated as a vessel, not a person. “I wish [I was a virgin],” she confesses to Dan. “It’s just, no one’s ever looked at me the way you just did. In fact, I don’t think they looked at me at all.”

As the season goes on, we get more glimpses of this old Serena, the “bad” Serena, the Serena who had multiple sex partners and did drugs and drank more heavily. In episode nine, Dan flashes back to the previous Thanksgiving, when he ran into drunk Serena on the street. Old Serena doesn’t dress like new Serena; in this scene, she wears an emerald-green dress, leopard coat, black tights and booties; her hair flat-ironed. In costume design, leopard print is sometimes used to denote tawdriness or sexual availability, so a whole coat of it tells us exactly how we’re supposed to see this old Serena: tackier, looser, wilder. (I mean, “Promiscuous” is playing in the background. These aren’t exactly subtle cues.) Unsurprisingly, the only gold on Serena’s body is a pair of earrings; though Dan is still drawn to her, she is not yet a fully realized fantasy.

Back in the present day (1.10), Lily convinces Serena to attend cotillion, pushed by her own mother, CeCe. CeCe even lines up a date for Serena, an Upper East Sider named Carter Baizen. Serena and Dan almost fall out when he tells her about her grandmother’s manipulations, but they end up reuniting at cotillion, the gold back of Dan’s vest matching Serena’s gold brocade gown and little gold earrings.

In episode eleven, they sleep together for the first time on Christmas Eve, Serena in a sequined dress, the cranberry color perfect for the holiday season; it may not be gold, but her necklace is, and sequins still give her a bit of Serena sparkle. Before they have sex, Dan presents her with the short story he wrote about her, about to be published in The New Yorker. It chronicles the first time they met, at a party freshman year—built up so much in Dan’s head that it’s become mythic, epic.

Serena and Dan’s relationship is not without tension; Dan often points out the privileges of being a van der Woodsen. When Serena confesses to breaking into Constance Billard’s pool (1.12), she receives a laxer punishment than the expulsion promised, her mother’s new fiancé, Bart, having secretly donated a new library to the school. In her meeting with Headmistress Queller, Serena wears a long-sleeved navy T-shirt, gray sweater vest, and her usual uniform skirt and loose tie. She normally pairs at least a white Henley or T-shirt with her uniform, and so further deviation—to navy—only highlights how different the rules are for Serena.

As much as the van der Woodsen name may serve her, Serena can’t quite escape the trauma that comes with it. In episode thirteen, Dan tells Serena that he loves her, and she avoids a reply—haunted, she later says, by the ghosts of her mother’s failed marriages. She asks him to explain why he loves her, and he tells her she’s “beautiful, smart, sexy as hell . . . [and] completely unaware of [her] effect on [him].” It’s a very One Direction understanding of love—two out of four things being her appearance, and the fourth being that she has no idea of the others. Still, with Dan’s reasons in mind, Serena is finally able to return the sentiment.

Their happiness, however, is short-lived: In episode fifteen, Serena’s old friend Georgina Sparks returns; Georgina, who “always brought out the devil” in Serena. Not wanting Dan to know Georgina, Serena begins lying to him, covering up where she’s been, wearing little of the gold or yellow or sparkles that light her up in his eyes. The night before the SATs, Serena goes out to dinner with Georgina, who drugs her soda. The next morning, she wakes up late and misses the exam; Georgina offers her blackout as a sign Serena hasn’t “changed as much as [she] thought.”

As Georgina reenters Serena’s life, Serena’s style can’t help but become tangled in her old friend’s. Georgina’s wardrobe leans rock-and-roll: lots of black, leather jackets, silver studs and chains. To their dinner, for example, Serena chooses a white top, tangled necklace, black pants and boots. On top, she wears a brown open sweater—like a new Serena piece—but with a silver-studded black trim—like a Georgina piece.

Serena tells Georgina never to contact her again, then doesn’t hear from her for two weeks—only to meet Georgina as Dan’s new friend, “Sarah,” and learn that she has an incriminating recording of her. After the Shepherd wedding, Serena went to Georgina, her tulle dress in hand, her gold slip almost covered by Nate’s white button-down—a shameful reminder of what they’d done together, her luminance stripped away.

Georgina, however, was secretly planning to make a sex tape of Serena and their friend Pete. Instead, the tape captured Pete overdosing, Georgina convincing Serena to abandon him in his hotel room as he died. From there, Serena got on a train to Connecticut, where she ended up at boarding school.

In the present day, Serena escapes back into her old ways, spending the night out drinking. When Dan wants to know where she’s been, she lies and says she cheated, and he breaks up with her. “I would rather Dan think that I cheated on him than know what I really did,” Serena tells her friends. “Dan puts me on a pedestal. If he knew the truth, he would never look at me again” (1.17).

With the help of her mother and friends, Serena comes to terms with Pete’s death and is finally ready to tell Dan the truth. Georgina gets to him first—stealing his phone and fooling around with him at the Humphreys’ loft.

With Serena’s honesty come the last gasps of gold and yellow: to the loft, she wears a navy dress, beaded necklaces, and gold trench. She still wants to fix things with Dan, to become that perfect girl again. She’s willing to overlook his hookup with Georgina, but Dan can’t move past her lies and scandalous past. At her mother’s wedding to Bart, they break up for good, Serena in a yellow floral bridesmaid gown with a black belt and gloves. “We’re exactly where we were at the Bass brunch,” she tells him. “I’m not who you thought I was and you can’t forgive that.” Yes, they’re in the same color palette but completely different worlds: Serena’s dress by Ralph Lauren, the flowers tying her to Lily and Blair. She decides to spend the summer reflecting alone in the Hamptons, Dan remaining in the city.

Season Two

Serena’s Hamptons wardrobe is easy breezy: lots of flat sandals, casual printed dresses, and cover-ups over swimsuits—including, naturally, a gold tunic over a black suit. She and Dan still miss each other, and when he comes to the Hamptons to find her, they reunite at the White Party.

Gold may not fit the White Party’s dress code, but Serena still looks like she’s stepped out of a myth; she wears a white Grecian gown with a large pearl cuff, silver chains threaded through her hair. The next morning, she and Dan decide to think about the reasons they broke up before they get back together.

Once they return to the city, Serena calls Dan and invites him to Blair’s party (2.2). Her outfit in this scene becomes her formula for the rest of the summer: instead of cover-ups and swimsuits, jeans and sleeveless going-out tops—in this case, white jeans and a Creamsicle-colored tank. As Serena talks to Dan, she picks an outfit for the event, holding up a honeycomb-print dress. Though she doesn’t wear the dress to Blair’s party, its cameo and their reluctance to delve into their issues foreshadow their breakup in the next episode.

On a walk in the park, Dan and Serena are confronted by the first appearance of the minis: preteen Gossip Girl readers who dress like their idols, Blair and Serena. The girls can’t believe that Dan and Serena are dating again, that they can forgive each other for their wrongs. While Serena wears her current go-to, a green sleeveless top and jeans, mini Serena is dressed in a little denim vest, orange tank top, and gray jeans, so much like an outfit that Serena wore at the beginning of her relationship with Dan, in episode 1.4. It’s almost as if she’s being visited by a Ghost of Serena Past, warning her not to repeat her mistakes.

Later that day, Serena and Dan break up in a stalled elevator, Serena wearing the honeycomb dress she almost wore the previous episode—only delaying the inevitable.

Their first day back at school is awkward, made more so by Dan’s flirtation with a new student, Amanda. Serena’s uniform is much like the previous year’s: a white T-shirt, cream-colored vest, loose tie, and plaid skirt. Her accessories, however, add new interest: in her hair, a printed scarf, and on her neck, a dart-shaped pendant. Serena wore similar scarves a few times in season one but rarely with her uniform; crown-like accessories were always the realm of Queen B and her headbands. As for the dart, Dan better watch out—once Dan goes on a date with Amanda, it’s war between the former couple.

Amanda was hired by Chuck, who hopes jealousy will drive Serena to take control and replace Blair as queen of Constance. His plan works: One morning, the minions are suddenly dressed like Serena, in loose ties, layered necklaces, and scarves. Serena herself wears a white T, loose tie, oatmeal-colored vest, and pink scarf. When she sees the flummoxed Blair, Serena unties her scarf from her hair and sweetly drapes it around her friend’s shoulders. Her power, the gesture seems to say, lies not in an accessory; she can bestow it upon whomever she wishes.

By 2.6, Serena and Blair are in a full-blown feud, fueled by Serena walking in Eleanor Waldorf’s fashion show with her socialite friends in episode five. Serena receives a personal invitation to visit Blair’s dream college, Yale—the inviting dean somehow enchanted by the publicity a girl like Serena could bring to his school, a three-hundred-year-old Ivy League institution. When Blair makes fun of Serena’s first choice, Brown, Serena decides to visit Yale instead, where she charms the dean over the more academically qualified—and less charismatic—Blair. By the end of the episode, Serena and Blair do make up, but not before Blair tells the dean about Pete and his overdose—a night Serena can’t escape, again and again. 

For her campus visit, Serena chooses a white-and-purple-striped schoolboy blazer with a gold crest, low-cut white blouse, jeans, and knee-high boots. The outfit is an interesting juxtaposition between how Serena wants to be perceived and how she is. She wants to be challenged and supported academically, to attend a college that wants her for her abilities—hence the collegiate blazer—but she has always been seen as a beautiful, passive object, something to be written about and desired—hence the low-cut blouse.

Unlike Blair or Lily, Serena rarely dresses in what the Upper East Side considers “appropriate” for an occasion. There’s always something slightly off, her dress a little too short, her neckline a little too low, a blazer thrown on top for decorum. Her new stepfather, Bart, wants to correct her and brings back a suit from his work trip to Paris (2.7): “conservative but classic,” as Lily describes it. He and Lily are setting new rules for their joined household—no going out on school nights and curfew on the weekends.

When Serena discovers these rules are motivated by Bart’s impending deals with some Midwestern executives, she goads him, going out to find some paparazzi in an orange halter dress and gold heels. The dress is probably the shortest she’s ever worn on the show, the message obvious: I know exactly what you think of me, and I don’t care.

At the Bass housewarming party, she sends this message again, this time with Bart’s gifted suit—no top underneath—and a tanked interview with InStyle. And yet, her sartorial rebellion leads to a real conversation with Lily about her parenting and a temporary peace among the van der Woodsens and Basses.

Over the next few episodes, Serena begins seeing Aaron Rose, a slightly older artist with an installation at Rufus Humphrey’s gallery. She can’t resist the chance to become a muse to a photographer, as she was to Dan as a writer. In 2.10, Aaron takes her portrait, Serena wearing a gray T-shirt dress with gold sequined sleeves and black tights. Her dress is not quite the full-on gold gown of season one, but the sequins show she certainly feels more sparkly, desirable, under his lens.

Serena soon learns that Aaron is polyamorous—with dates and subjects—and breaks it off, but a conversation with Blair begins to change her mind:

Blair: Beneath that free spirit façade, you’re totally conventional, just like I am.

Serena: It’s not a façade. I believe in freedom, people following their hearts, doing what they want; you know I always wished I’d lived in the sixties.

Blair: You believe in long hair, peasant skirts, and sandals, but you in an open relationship, I don’t think so.

Blair sees Serena’s image in stylistic terms—an embracement of hippie fashion rather than ideals. So it’s appropriate that, when Aaron shows up at her penthouse and says he thought she didn’t want a life like their parents’, Serena makes an unconventional outfit choice: she throws a plaid trench over her nightgown and takes him for a walk in Central Park. The coat is the same one she wore when she agreed to her first date with Dan—a reminder, perhaps, that Serena would rather be in a monogamous relationship with him.

The next episode is also the next instance of Serena pairing a button-down with her uniform. Sure, the shirt is rumpled, and she’s wearing it with a brown leather vest and loose tie, but the choice is a little more mature, controlled, like she’s trying to appear in Aaron’s eyes.

Indeed, later that day, he says he wants to close their relationship. She’s delighted, so much so that when Aaron tells her he’s sober, she lies and says she doesn’t drink either.

Still, she can’t hide “old Serena” for long, even if she asks Dan and Chuck not to talk to Aaron about her partying days. To their Thanksgiving dinner, she wears a red-and-orange minidress, short enough that Chuck makes a skeevy comment, the color and hemline reminiscent of the orange halter dress from a few episodes before. Aaron realizes that Serena is lying, but instead of rejecting her, as she likely expects, he asks her to tell him about her past.

Lots of things happen over the next few episodes: Bart dies in a car crash, Serena breaks up with Aaron and reunites with Dan, they discover they share a half brother. Her clothes don’t stray far from solid browns and blacks and grays—perhaps out of mourning for her stepfather, more likely out of mourning for her doomed second try with Dan.

Dan hopes they’ll attend Yale together, but on admission day (2.16), when they both get in, Serena secretly gives up her spot for Blair, who has been wait-listed. Her uniform is divided between her two loyalties: her collegiate plaid blazer much like Blair’s but its muted color palette more in line with Dan’s.

Later that day, she and Dan attend the opera with their parents, now dating each other, and see the world of kissing stepsiblings that awaits them. Serena, as for many of her most formal moments, wears a yellow gown. At the end of the episode, she stares wistfully at a photo of herself and Dan at cotillion, the days of her gold dress long gone. Dan, too, is drifting away, beginning an inappropriate friendship with Serena’s Shakespeare teacher, Miss Carr.

As Dan and Miss Carr grow closer, Serena starts to dress more like Dan and, for that matter, Miss Carr—gray and black solids and stripes, even a black cape-like coat. Miss Carr admires Dan’s writing, and Serena can’t help but worry about her own, to try harder to prove that she is serious and literary, even if it is only through her clothing. After all, as she tells Miss Carr, her mother never gifted her a notebook for her writing but “a Chanel wallet and a credit card to get [her] out of the house” (2.17). Serena is intellectually insecure, as anyone would be if they were constantly praised for things as ephemeral as beauty or sexiness; she’s been taught to express herself through buying and wearing clothes.

After Blair spreads a rumor that Dan is sleeping with Miss Carr, Serena provides a photo that confirms her story: Dan comforting a crying Miss Carr at a café. Miss Carr is fired, and Dan and Serena break up—turns out, Dan and Miss Carr hadn’t yet slept together. Serena attempts to apologize to Miss Carr, delivering a heartrending line: “You’re the only teacher who’s ever expressed any interest in me.” You have to wonder if that’s why Serena seeks out artists and writers, some outer intellectual validation that she is worthy of study, if not her own creation.

In the next episode, for example, Serena harbors a crush on Julian, the wunderkind director of her school’s production of The Age of Innocence. Her crush is reflected in her fashion choices: a skinny silver scarf to mimic his, paired with a black top and gray cardigan. She’s always trying to be a muse to creative men, to take on their talent instead of nurturing her own, and in the end, Julian barely knows who she is, calling her “Sabrina.” (Come season five, that name will take on even more significance.)

In episode twenty, Serena runs into her socialite friend Poppy, introduced in 2.5. When Poppy learns what Serena’s been up to since, she looks at her sadly: “A girl like you,” she says, “should be on the arm of a designer at the costume ball one day and yachting around the Maldives the next, not making up and breaking up with the same high school boy and feuding with your frenemy.”

Serena tries to end her “rut” by throwing Jenny the sweet sixteen she doesn’t want, all while dressed in a long-sleeve gray dress with sequined neckline, shiny gray tights, and a silver heart-and-dagger pendant. She may have a little sparkle around her neck, but she’s still in dejected gray, second-best silver—the party quickly turning from the social event of the season to a high school rager. 

Poppy invites Serena to Spain, and Serena agrees, eager to escape the wreckage of her party. At the airport, she meets Poppy’s boyfriend, Gabriel, for the first time—though he swears it’s the second. He says they met the night she was drugged by Georgina.

In this scene, Serena wears a yellow leather trench over a gray top and gold necklaces. Again, it’s not quite the gold dresses of season one, but it’s a step closer, a bright, attention-grabbing coat, not a drab gray dress. The coat speaks to the sad pattern of Serena’s life—that change will come not through her own will but through the desire of a man. By the time they return from Spain, Gabriel has moved from Poppy to Serena.

Gabriel is unlike Serena’s previous love interests—not an artist like Dan or Aaron or Julian but a businessman. Like her mother, who traded “rock stars for billionaires,” Serena is moving from creative types to moneyed types, from men who can validate herself to men who can validate her place in this world. Lily, of course, approves of Gabriel and even encourages her co-op board to invest in his company. Unlucky for them, Gabriel is a scammer, secretly in cahoots with Poppy. When Lily finds out, she insists on quietly paying everyone back rather than going to the police, and when Serena won’t follow her plan, she has her daughter arrested.

Serena’s outfits during these episodes shift slightly, favoring a slightly more rocker look—leather jackets and tanks and jeans. In fact, she looks a little more like Georgina in season one, appropriate considering the lie Gabriel told about meeting them that night.

Thanks to her arrest, Serena has become a paparazzi target (2.25). They follow her to her pre-graduation breakfast with Blair, Serena wearing a bright blue halter gown, later braiding a green tassel in her hair rather than wearing a mortarboard. Oh, Serena—never change. 

During the ceremony, Gossip Girl drops her present for the senior class—a label for each of the main characters. “After today,” she writes, Serena is “officially irrelevant.” There’s no greater insult for Serena—a girl who is always the center of attention, the muse; who was the original inspiration for the blog itself. Gossip Girl’s first post was about Serena, her white dress soaked on a field trip to the Intrepid.

Serena decides to figure out Gossip Girl’s identity, even invites the blogger to meet her at a bar later that evening. Instead, every senior, starting with Dan, shows up—Gossip Girl messaged them all. Serena wears a burgundy-sequined strapless dress, the color and sparkle not unlike the dress she wore the night she and Dan had sex for the first time, the night he gave her a copy of his story.

Dan dismisses her worries of irrelevance: “Without Serena van der Woodsen, who would I have dreamt about?” Serena smiles at this, her existence once again justified by Dan, by his fantasies and stories about her.

Reinvigorated, she packs for a summer in Europe before her freshman year at Brown, her outfit a spangly tank, jeans, and booties, a blue leather jacket thrown on as she waits for a taxi. There, she runs into Carter; he’s found what she’s long been looking for: her absent father.

Season Three

Serena spends the summer partying across the globe, all while hiding her exploits from her family. She and Carter did find her father, but when he didn’t want to see her, she decided to become inescapable, a tabloid fixture. Her wardrobe, too, suddenly seeks the attention she craves. Season three Serena, says Daman, is a return to “the old party-girl Serena, that girl who kind of overdoes it a little and is trying to get attention through her clothing” (“Gossip Girl Style with Eric Daman”).

She returns to New York, still pursued by the paparazzi and Carter. While she’s happy to be photographed, she’s avoiding Carter, who wants her to stop justifying her father’s rejection. To escape Carter, she undoes the ties of her pale blue halter dress, attracting the paparazzi with her wardrobe malfunction.

Carter follows Serena to a polo match, where her infamy has somehow earned her the first ball throw. There, she wears a Grecian gown, much like the one she wore to the White Party a season ago. The color, however, is an eye-catching orange, perfect for stealing a horse and riding it in front of photographers.

By episode two, Serena is having doubts about Brown. She doesn’t know what she wants to do with her life—and, I think, doesn’t know how to live outside New York, a city where everyone knows her name. Instead of leaving for Providence, she crashes at Chuck’s apartment and quickly ruins one of his business deals. “Train wreck,” he mutters, and almost as proof, she takes Carter to interrupt another of Chuck’s business meetings, this time at a bar. Again, she goes for solid, bold color—a cowl-neck royal-blue dress and layered gold necklaces. This is old Serena at her peak, reminiscent of the bright green dress she wore in the Thanksgiving flashback.

In episode four, Lily returns from taking care of CeCe, and Serena must finally tell her that she’s deferred Brown for a year. Suddenly, Serena is dressed like she’s in early season two: a brown tank and jeans, a very Lily-like turquoise necklace. It’s as if she’s trying to prove, through her wardrobe, that she’s not old Serena, that’s she’s still the Serena who received a personal invitation to Yale.

To show her seriousness to her mother, Serena interviews with Tory Burch, Marchesa, and John Porto Gallery. All reject her; as Serena says, they’d rather she attend their parties than work for their companies. For all her interviews, she wears a gray blazer thrown over a gray tank, lavender bandage skirt, lots of red beaded necklaces, and lipstick—a rare formality for Serena. She looks as if she’s approximating office wear, as if she’s pieced together a look from her usual clubbing and casual wear. After all, none of the close women in her life work—not Blair or CeCe or Lily.

At lunch, however, Serena meets a publicist, K.C., and impresses her with her deft handling of her client. Suddenly, Serena has a job that makes use of her fame, her connections. She even works a premiere in a silver-sequin bandage dress, a gray blazer on top. Her professional style, from here out, is “throw a blazer on it!”

Serena parlays her PR experience into a job working for Nate’s cousin Tripp van der Bilt (3.9), recently elected to Congress and married to Maureen. For the interview, Serena wears a variation of her first interview look: a black blazer, tank top, chunky statement necklace, and miniskirt. Just as her first job was a way to prove herself to Lily, this job is a way to get closer to Tripp. What kind of PR professional is Serena, anyway, when she’s about to participate in a public relations nightmare?

Serena and Tripp flirt for a few episodes, kissing after Tripp discovers one of Maureen’s machinations. All three attend Thanksgiving dinner at the van der Woodsen penthouse (3.11), the outfits from which I discussed more thoroughly in Lily’s profile. Lily is disappointed in her daughter for seeing a married man but not as disappointed as Serena is when she finds a letter from her father. Lily was with William that summer, when Serena was trying to see him.

Serena and Tripp run away to the van der Bilts’ country house; Tripp is planning to divorce Maureen. She gets to him first, asking if she can present an idea to Serena (3.12): she’ll stay Tripp’s wife, and Serena will become his mistress. “It’s a time-honored political tradition,” Maureen explains. “I’m Jackie [Kennedy]. You’re Marilyn [Monroe].” When Serena objects, Maureen shows her the letter from William, wondering how Rufus will react to discovering Lily is a “cheating whore.”

The scene’s outfits only reinforce Maureen’s proposed roles. She is Blair-like, practiced, precise, in a structured hat, tailored green coat, and plaid scarf; Serena is soft, sensual, in a low-cut gray sweater, tan jeans, gray shawl, gold necklaces, and diamond studs—the same ones, I think, that she wore in the Thanksgiving episode, that remind the viewer of Lily. Maureen sees them as one and the same, as temptations and home-wreckers.

After Tripp almost kills her in a car crash, Serena turns to Nate, who’s long been waiting to date her. They begin seeing each other in episode thirteen, but Blair advises Serena to take things slow. Their conversation is riddled with talk of “control,” of Serena as a sundae that Nate will gorge himself on after years of hunger.

In episode fifteen, Jenny decides to lose her virginity to her drug-dealing boyfriend, Damien; both Nate and Serena try to discourage her. Unaware he’s on speakerphone, Nate tells Blair that losing her virginity is a “huge deal for a girl like Jenny”—implying to the listening Serena that it wasn’t for her. In this scene, she is getting ready for an event in a black slip and gold robe, the color calling back to the dress she wore when she and Nate first slept together.

Serena changes into a black lace dress, not unlike the one Jenny is wearing—a sympathy between them, a common public obsession with their purity. Stories of Serena’s sexual past keep following her, tainting her present relationships:

Nate: Everyone knows the stories about Adam Handler, Jake Henderson, Matt Price, the art teacher from Prague.

Serena: I didn’t sleep with all those guys, Nate. Haven’t you heard of locker-room gossip? They lied or exaggerated.

Nate: Serena, I lost my virginity to you on a bar at the Campbell Apartment.

Serena: And somehow that reflects poorly on me and not you? Talk about a double standard.

Though Serena and Nate make up by the end of the night, distrust follows them for the remainder of the season. In episode eighteen, Nate discovers that Serena has been secretly meeting Carter. She hasn’t yet told Nate that she’s still looking for her father, and he assumes the worst. Serena even leaves a wedding to follow Carter to Palm Beach, abandoning him once she learns that he’s been stringing her along, hoping they’ll get back together. Her look for the wedding—a blue long-sleeved dress with a white-and-green beaded necklace—is much looser and more conservative than usual, as if she’s trying to convince Nate that she’s not what he thinks she is.

The outfit becomes even more significant when Serena arrives at her father’s Palm Beach hotel room. The door opens to reveal Lily, mirroring her daughter in a V-neckline and green beaded necklace. It was Lily, not CeCe, who was sick last summer, and she’s come to William for her six-month checkup.

By episode twenty, Serena is back in New York, happy again with Nate and bonding with her father. For brunch at the penthouse, she’s bright in a turquoise sheath and pink earrings, coordinated with Lily’s own bright pink sheath. When William asks her about boarding school, she lies about her wild days there, worried that her father won’t love her for all she is. At the end of the episode, she finally tells the truth, and he allays her fears.

Because who is William to judge? He has his own secrets, chiefly lying to Lily about her relapse so he can remain close to her. He even conspires with a co-op member to say Rufus cheated on Lily—all the proof Serena needs that her parents should get back together (3.21).

Serena attends a gala at the New York Public Library, her parents in tow. She’s angry at her friends, and especially Nate, for being suspicious of William. For the first time since season one, she wears a full gold dress, ascending not just to another’s fantasy and desire but to her own: the dream of a perfect, whole family, a loving, admiring father.

When William realizes his secret is about to be revealed, he skips town. Serena goes after him, not believing that he would leave her again. She lets him go before the police arrive—called, against her will, by Nate.

That night, Serena turns to Dan for comfort, drinking and kissing at the Humphrey loft. When Nate finds out, they break up, Serena left to decide if she wants to mend things with him or start over with Dan.

As she and Dan wait at the hospital, Blair’s maid Dorota in labor, they look at the babies in the nursery, baffled by the fresh starts before them. Dan points to one: “She’s going to grow up to have fabulous hair and a great smile, but her daddy issues are gonna make it real hard for her to trust people.” And I mean, who could resist that? The fantasy of Serena is slowly starting to flake, to reveal the real pain beneath her golden exterior—all reduced to two body parts and a man’s absence.

Season Four

Blair convinces Serena to spend the summer in Paris—Blair ruling the Right Bank, Serena the Left Bank. Serena occupies herself with Parisian men—becoming, as Gossip Girl wryly notes, “a muse to us all.” This line is layered over a shot of Serena in an oversize striped button-down, sketching a naked man; any artistic interests still defined by her interest in men.

Though the shirt is likely borrowed—much like Nate’s button-downs in season three—her other fashions are singular. Daman went all out for the Paris episodes, dressing the girls in bright and glittery designer confections. Take, for example, this sharp-shouldered gold blazer, paired with a white striped tank and bright blue pants.

And yet, Serena’s story lines in Paris are very much rooted in New York: Should she choose Dan or Nate? Should she go to Columbia—her father’s alma mater—even though Blair is transferring there? While Blair eventually agrees to the latter question, the former is answered for Serena—when she gets back to the city, Dan is dating his longtime friend Vanessa, and Nate is dating a new girl, Juliet Sharp.

Juliet is a fellow Columbia student and the key master at Hamilton House, an exclusive on-campus society to which Blair wants admittance. On their first day at Columbia (4.3), Serena and Blair go to Hamilton House, hoping to both receive a key necklace—Serena in a brown-and-pink patterned dress and woven belt, in step with Blair’s own brown dress. Juliet, however, says she has only one key left—and it’s Blair’s.

The key itself is a silver Tiffany pendant, more in line with Blair’s taste than Serena’s, but the rejection still hurts. Serena suspects Juliet is withholding her key, and when she confronts her, Juliet says that Blair told the Hamilton House alumni committee about Serena’s “sex tape”—much as she did when they visited Yale. Yet again, the night of the Shepherd wedding follows Serena. Blair and Serena soon learn that Juliet is lying, and Serena receives her rightful key. The friends believe Juliet is jealous of Serena’s past with Nate—but as we’ll discover, Juliet’s revenge goes so much deeper than that.

Serena is repeatedly late to class thanks to a man who steals her cabs to send off his one-night stands—and flirts with Serena in the process. When Cab Man first appears (4.5), Serena wears a bright yellow vest-like top, yellow flower hairpin, blue shorts, and gold chain necklace—the return of Serena in yellow signaling desire.

Later that day, Gossip Girl sends out a blast saying Serena has an STD, and Serena suspects Juliet submitted it. Serena begs Nate not to get tested right away and confirm the rumor, but then another blast drops with a photo of both Dan and Nate at Columbia’s health clinic.

When Vanessa sees the photo, she confronts Serena, accusing her of sleeping with Dan that past spring. “Let’s just say it wouldn’t be the first time a guy has lied to his girlfriend to cover up a night spent with you,” Vanessa says—alluding, of course, to the first time Nate and Serena slept together.

That evening, Serena attends a party at Hamilton House in a cream cocktail dress with gold trim. More importantly, she’s wearing diamond studs and a bun—the pairing she goes to when she wants to be her most proper, most Lily-like self. She wants to prove to her classmates, to her professors, that the rumor isn’t true, that she is unsullied. For that is the implication of Vanessa’s reaction—that Serena’s supposed STD is a mark of her immorality, her sleeping with Dan and Nate when they were dating other girls.

At the party, Juliet steals Serena’s phone and sends an email to her professor, offering sex for grades. When the dean and professor confront Serena with the email, Juliet sets up Vanessa to take the blame.

Serena heads back to the Upper East Side, where she runs into Cab Man at a bar; they spend the night talking. “I thought I could start over,” she tells him, “[but] my past seems to follow me.” Indeed, Cab Man—or Colin—is also a reminder of her past, of a relationship with a teacher that almost went too far. As she discovers the next morning, Colin is the professor for her new business class.

Serena plans to drop the class and date Colin until Lily shames her into taking it (4.6), needling her daughter’s intellectual insecurity by implying the subject might’ve been too difficult for her. Serena and Colin agree to pause dating until the class is over; they get to know each other through regular office hours, Serena throwing a tan blazer over her body-con blue dress (4.7). As it was in season three, her blazer is a stab at professionalism, her seriousness as a student, even as she and Colin struggle to wait six weeks

At Blair’s birthday party, they almost break their agreement, Serena yet again in a yellow gown and giant gold necklace, bright against the other main characters’ dark reds and purples and blacks. By the next episode, Colin quits his class for Serena, kissing her in front of all of society at the New York City Ballet. Juliet tries to use their relationship to get Serena expelled, but Serena’s friends rally around her instead. She and Colin ultimately break up, and Serena is presented with the same question from the summer—Dan or Nate, both recently single.

Serena struggles to choose between the two men and even between two dresses for Chuck’s Saints and Sinners party (4.9). Ultimately, she goes with Saint in a lace mask and gray-blue Carolina Herrera gown, the color tying her to the one she really wants—Dan in his light gray suit. Unfortunately for Serena, Juliet and Jenny are also wearing the dress; they’ve teamed up with Vanessa to impersonate Serena at the party: Juliet kissing both Dan and Nate; Jenny humiliating Blair. Unbeknownst to Jenny and Vanessa, Juliet is planning an even crueler revenge; at the end of the night, she drugs and dumps Serena at a motel.

When Serena is found a few days later, Lily checks her into the Ostroff Center (4.10); everyone except Dan believes that old Serena has returned. “She’s not just the beautiful teenage girl you saw at some party anymore,” Lily tells Dan. “She’s a troubled young woman avoiding some very real consequences.”

Serena, too, has difficulty believing her behavior, though she notes it’s not without precedent. In therapy (4.11), she says, “This wouldn’t be the first time I’d been with two guys in one night or betrayed my best friend.” The scene flashes back, as expected, to the Shepherd wedding, to Serena running away to boarding school. For the first time, we receive glimpses of her life, her wardrobe, at Knightley.

Like Constance, Knightley has a uniform, which appears to include a blue button-down and red-and-gold tie. Serena wears her tie loose, her shirt collar undone, layered with a sparkly blue cardigan, gray tweed shorts, and diamond-patterned tights. She’s still the wild Serena we saw in the Thanksgiving episode, drinking absinthe and paying her classmates to do her homework. That is, until she meets Mr. Ben Donovan—save for Miss Carr in season two, the only teacher to take her seriously as a student.

Around Mr. Donovan, Serena’s ties are still loose, but she wears them with collegiate blazers and plaid button-downs, mirroring his. It’s almost like she’s trying to look the picture of the perfect prep school student to impress him, to show him she wants to do well.

One day, Ben drives Serena to Vassar Library; his car breaks down in the rain. They stop at a bed-and-breakfast for help, and Serena asks him if they can get a room. He turns her down—becoming, perhaps, “the only guy to say no to [her],” as she later tells her therapist.

In this scene, she wears the standard Knightley blue button-down with a black-and-gray argyle cardigan. Reader, I gasped—an argyle cardigan being the same piece that Dan and Serena traded back and forth in season one, that Miss Carr wore after she had sex with Dan in season two. This piece is drawing parallels between the stories, between these two inappropriate teacher-student relationships.

Still, not everyone believes that Mr. Donovan said no. When Serena returns to the city, Lily tries to get her daughter back into a private school, but no one will take her after seeing her dismal records at Knightley. Lily uses a rumor about Serena and Mr. Donovan as leverage against Knightley, not realizing that the school will take criminal action. She forges her daughter’s signature on an affidavit, and Ben Donovan goes to prison believing Serena has lied. Hence, he and his sister, Juliet, take revenge on Serena, aiming to leave her with as little as Ben has.

Once Serena learns what her mother did, she visits Ben in prison, wanting to do whatever she can to help him. Lily, too, works to get Ben out on parole—having believed, all this time, that the rumor about her daughter was true. The Humphreys offer Ben a room at the loft, and Serena strikes up a friendship with him, even begins dating him in episode fifteen.

Throughout these episodes with Ben, Serena wears a lot of grays and other neutrals paired with more glittery elements—the former meant to soften and dull the latter. In episode fourteen, for example, she wears a gray vest over a gray sweater and sparkly skirt, rhinestone necklaces on top. As much as she tries to relate to Ben, to his more humble background as a Knightley townie, she is still the daughter of the woman who put him behind bars, and she can’t help but remind him of the wealth and privilege that brought them to this point.

Ben and Serena ultimately break up, and Lily turns herself in for her forgery, her sister, Carol Rhodes, sweeping into town with her own daughter, Charlotte (4.18). Carol raised Charlie in Florida to shield her from the Upper East Side, and Serena is determined to show her cousin another side to her world. She even gives Charlie the necklace off her neck—a “family heirloom,” she says. Naturally, it’s gold.

Charlie stays in the city and quickly learns to navigate Gossip Girl; she helps Serena follow Dan and Blair, whom she suspects are seeing each other (4.19). They’re really only friends, Blair secretly dating a prince of Monaco, but Serena is still angry at Blair, sure that any appeal Dan has for Blair is only because he is “hers.”

“You would see it that way,” replies Blair, “because it’s always about you, isn’t it? I’m sorry to break it to you, but Dan and I have a real connection. We did things like visit the Dia and debate Chabrol versus Rohmer. Things we could never do with you.” Just as Lily did earlier this season, Blair strikes one of Serena’s deepest insecurities; she may inspire art, but she lacks the knowledge, the confidence, to speak to it.

Charlie begins seeing Dan, which, strangely enough, seems to bother Serena less than the idea of Blair dating Dan. That is, until Charlie steals Serena’s most iconic dress, her gold cotillion gown, to attend a Constance fundraiser with Dan. Serena herself is in a coral gown with silver accents and earrings, only second-best.

At the fundraiser, Serena runs into Headmistress Queller, who is disappointed to learn that her old student is attending Columbia, not Brown. “I know I was always hard on you, Serena,” says the headmistress, “but it was only because I thought you could become something. I’d hoped you’d leave New York, see the world. Maybe find your place somewhere far away from all this.”

Soon after, Serena is accosted by the minis, now all dressed as little Blairs. “How could you not end up with Nate or Dan?” asks the one who once dressed like Serena. “I used to want to be like you, but now I want to be like Blair.” In the halls of her old high school, Serena is haunted by her past mistakes, culminating in a confrontation with her doppelgänger, Charlie.

Charlie, Serena learns, has stopped taking her psychiatric medication; she finds her cousin in a classroom upstairs, a window open. It’s like Serena is staring at her high school self, Charlie’s hair done in a simple ponytail, just as Serena did hers. Only Charlie’s earrings are different; she chose a larger statement earring, more at home in the current Serena’s jewelry box. 

“[Being me] doesn’t mean what you think it means,” Serena tells her cousin. “All night, I’ve realized I didn’t choose college. I never chose between Dan and Nate. I didn’t even choose Paris last year.” She’s repenting to the girl she once was, who made active choices. Charlie climbs down from the window and comforts her, and they return to the penthouse together. Little does Serena know, Charlie is actually Ivy Dickens, an actress hired by Carol to gain access to her daughter’s trust fund. Charlie’s mental health struggles were all performed, meant to prevent the family from seeking her out in Florida. 

Serena decides to stay with CeCe in California for the summer: “I needed to make a choice,” she tells Blair, “and I choose me.” On a beach, a sarong and denim jacket over her suit, she comes across a man reading her favorite book, F. Scott Fitzgerald’s The Beautiful and Damned. (“I relate to it,” she says, “more than I should admit.”) 

The man, Marshall, is scrambling to put together a scene-by-scene comparison of the book and movie script for a meeting, and she offers to help. Then the director, David O. Russell, appears and gives her a job—calling Serena “the beautiful” and Marshall “the damned.” Serena’s finally found work from, yes, her beauty and timing, but also her own knowledge and experience—a sign, perhaps, of promising things to come. 

Season Five

The season opens with Serena still in California, working on the set of The Beautiful and Damned. California Serena is thriving in bright oranges and yellows, sunny colors for the summer weather. For example, she wears this pink-and-yellow printed dress in episode one, paired with yellow and orange necklaces. Big necklaces, says Daman, are season five Serena’s new “statement piece. . . . We’ve toned down the clothing and amped up the jewels” (“5 Years”).

Serena has a potential new mentor in one of the movie’s producers, Jane, and a jealous supervisor, Marshall. When Serena finally meets with Jane, she learns that Marshall took credit for the comparison she wrote at the beginning of the summer. Jane asks Marshall to give Serena more responsibility, and so he gives her his entire task list, sure she won’t be able to finish it that day. Her last task is getting the film’s star some medical marijuana—marijuana, she soon learns, that he isn’t allowed to have or the movie will shut down. 

When she confronts Marshall, he accuses her of showing him up. “I need this job more than you do, okay?” he says. “I pay for my life. . . . You do one lap around this party, you’ll get ten job offers. You weren’t even looking when you found this one. In two weeks, when you’re at college, will you even look at this as anything more than that thing you did that summer?” Guilted, Serena offers to clean out her desk. 

The next day, when she goes to get her things, Jane offers her a job with her production company; she sees something in Serena that she can’t yet see herself—a talent, a purpose, that Serena’s never had before.

Serena’s color palette carries over to an unexpected character: Ivy Dickens, now auditioning for roles and living with her boyfriend, Max, in Los Angeles. Serena runs into Ivy at a café and, still believing her to be Charlie, convinces her to come back to New York. Caught in Carol’s lie, Ivy quickly cuts ties with Max and moves out (5.2). In this episode, Serena wears a gray striped tank and floral-print skirt, topped with a coral blazer and dangly earrings. Professional Serena is back, a blazer the solution to any outfit. Ivy keeps things more casual but picks up Serena’s coral tones in her jeans and hat.

Serena and Ivy return to the city in episode three, and Serena helps Jane set up her New York office. She’s flourishing in her new role, still wearing her sunny color palette—even convincing the reclusive Daniel Day-Lewis to consider one of their scripts. That is, until Dan’s first novel, Inside, is published, the characters based on his friends and family (5.4). Before Blair and Serena read it, both assume Serena is the focus, as she was in Dan’s New Yorker story. “Every girl needs to be knocked off her pedestal a little,” Serena jokes. “Can’t handle that kind of pressure.”

And knocked off her pedestal she is. Claire Carlyle is the real star of Dan’s book, while Sabrina von Sloneker is a “dreamy blonde with . . . legs” for which “everything comes easy.” She’s “glamorous, sexy, beautiful” but also “selfish, insensitive, shallow.” She’s Dan’s fantasy wrapped around the reality he could never handle, a muse undone. To quote Taylor Swift, “Darling, I’m a nightmare dressed like a daydream.” The cherry on top is “Sabrina,” the name her crush Julian once dismissively called her.

Serena, of course, is furious with Dan. “In high school, you were the only one who saw me for who I really was or who I wanted to be,” she tells him. “You helped me be somebody that I was more proud of. Do you even remember the girl you fell in love with? Or just that she got so drunk on Thanksgiving that she got grazed by a taxi . . . or slept with not one but two of her professors?” Serena’s past continues to follow her, now into her work life. Her fellow assistant believes she’s Sabrina, Daniel Day-Lewis drops their project, and Jane says she can save her job by getting the film rights to Inside.

The next episode, Serena has dropped her California color palette and reclaimed her sparkly pieces—as if she’s realized she can’t reimagine herself, can’t escape the image that others have created of her. To breakfast with Dan, Serena wears a silver-sequined teal shirt, striped skirt, and teal jeweled earrings. There, she fake apologizes to Dan for her reaction to his book, hoping he’ll agree to let Jane’s company produce the movie. Though they do ultimately reconcile and Dan does give her the rights, Serena never quite receives what she wants. Dan, now in love with Blair, remains unconvinced that Serena is the love of his life—as he is for her.

In episode six, Serena learns that Jane wants to turn Inside into the next Social Network—and “Zuckerberg” Dan in the process. Worried, Serena asks Jane’s old friend—newspaper mogul Diana Payne—for help. Diana reminds Jane of their shared history to convince her to drop the film. Considering that Diana is later revealed to run a brothel, I’m inclined to think Jane was once a sex worker, her past trailing her just like Serena’s trails her. Even their outfits mirror each other’s: both in one-shouldered dresses and dangly gold-chain earrings, Serena’s teal and Jane’s purple and black.

Diana, however, gets just what she wants: she convinces the now-jobless Serena to write a blog for her newspaper, The Spectator. Through her own writing, Serena can take back her narrative from Gossip Girl and Inside.

Outside the Spectator offices, Serena meets Ivy’s old boyfriend, Max—in the city for a job interview. After a flirty chat, and at Diana’s encouragement, she invites him to a production of Sleep No More. While Serena waits outside, believing Max has stood her up, Diana secretly sends Max in, telling him that Serena is wearing a “beautiful gold dress.” The actual girl in the gold dress? Ivy, of course.

Max slowly pieces together Ivy’s deceptions, all while beginning to date Serena. He even shows up at the penthouse the night of CeCe’s Studio 54 party, the Rhodes women dressed in seventies-inspired metallics and sequins. Serena herself is in a giant gold necklace and draped gold dress, as if she’s finally wearing that “beautiful” dress that Max was looking for. When Max tries to convince the family that Ivy is not Charlie Rhodes, Ivy says that Max is blackmailing her with a sex tape; she is worried, she says tearfully, that he will do the same thing to Serena. It’s a perfect lie: tinged with the threat of revenge porn, sympathetic to Serena, whose past is constantly used against her.

After her “close call” with Max, Serena reflects on her dating history. As she tells Dan: “I thought I changed my ending by getting the job with Jane or this blog, but the truth is, I’m still making horrible decisions in my love life.” Dan advises her to look through Gossip Girl, and when she does, she realizes that she never got things “right” before or after Dan. 

Blair, meanwhile, is about to marry her prince, Louis. When he suspects that Blair and Dan are having an affair, Serena covers for them, saying that she and Dan are secretly dating. Louis believes her and Serena gets what she wants—an excuse to stay close to Dan until Blair’s wedding.

Bubble Episode

I had many options for Serena’s bubble episode, but I kept coming back to 5.13, “G.G.” I felt odd, at first, choosing Blair’s wedding episode for Serena’s profile, but in many ways, the episode is as much Serena’s as her best friend’s.

Let’s start with the opening scene: Serena’s first and only dream sequence. Blair often dreams herself into Audrey Hepburn movies, but Serena imagines herself as a different star, the one Maureen once compared her to: Marilyn Monroe. In her dream, Serena lip-synchs to Marilyn’s “Diamonds Are a Girl’s Best Friend”; the men dancing around her include Louis, Nate, Chuck, and Dan. When Dan sees Blair, dressed as Holly Golightly in Breakfast at Tiffany’s, he breaks away from the group. Serena tries to pull him back, but he escapes her grasp, ascending the stairs to Blair.

Serena’s costume is not an exact replica of Marilyn’s but a high-fashion assemblage of its components: pink strapless gown, pink opera gloves, and piles of diamonds. Tom and Lorenzo wrote an excellent analysis of the gown and its legacy, and unsurprisingly, the dress is loaded with sexual symbolism:

 It’s a gown that speaks of sex and femininity even as its wearer sings a song about money and security. We could get into the long history of pink in costume design as a coded color for femaleness (or as an even more coded reference to the vagina). We could talk about the history of the opera glove on-screen and how it was a shorthand for a sexually available woman. . . . Suffice it to say, Marilyn is practically clothed in over a half century of tropes denoting female sexuality here.

The men are dressed identically in white tie, as they were in the original scene. But unlike in the original, the men aren’t just a bunch of random hunks—they’re men whom Serena knows, some of whom she’s dated. In Serena’s subconscious mind, the men in her life are there to worship her, to desire her, to serve her; no man has ever wanted Blair over Serena, especially not a man as important to her as Dan. He’s supposed to choose the Marilyn, not the Audrey (funny, considering Marilyn was Truman Capote’s choice for the role of Holly).

Serena wakes in a silky platinum-colored nightgown and robe, almost blending back into her sheets and the dream she’s still absorbing. It’s the morning of Blair’s wedding, and she changes into a striped gray-and-pink sweater and pink printed dress—the touches of pink calling back to her dream and hinting at the day ahead. As Serena stands at the top of the stairs, looking down the excited Louis, Dorota tells her that one day she’ll find a man who loves her as much as Louis loves Blair—and then Dan walks in. Unlike in the dream, neither ascends or descends the stairs—Dan only stares up at her, high on her pedestal, as he did on their first date.

Serena changes into her maid of honor gown and matching fascinator—pale pink, like the lesser bridesmaids’ dresses, but longer to show her status. The color matches the wedding’s flower, peonies, but also reminds the viewer of Serena’s dream.

Seeing Blair’s doubts over her wedding, Serena tries to convince her that she should be with Chuck—that Chuck is to Blair as Dan is to Serena, that they always come back to each other. Even after Gossip Girl posts a video of Blair declaring her love for Chuck, Blair goes through with her wedding. Serena, however, doesn’t give up on Dan, telling him she still loves him: “Always have, always will.” Dan doesn’t have an answer for Serena and instead helps Blair escape the reception—going up some metaphorical stairs, if you will.

By episode fifteen, Blair is playing Cupid, her ill-fated marriage to Louis having sapped any romance from her life. When both Dan and Serena tell her that their last good Valentine’s Day was with each other, Blair sets them up. She cancels their plans at the same restaurant so they’ll eat together, even hires an older couple to tell them how cute they are. Despite Dan’s rejection at the wedding, Serena is still in love with him, her interest apparent in her Humphrey plaid sweaterdress, much like something she would’ve worn in season one.

Even the fake couple calls back to season one Derena (and, in my opinion, When Harry Met Sally . . .): the man in an argyle sweater with a plaid shirt, the woman in gold jewelry. Though Dan and Serena soon figure out Blair is behind their setup, they agree to attend Nate’s Come As You Were party with her—the dress code is their high school uniforms.

Serena, of course, wears her plaid skirt and loose tie with a white tank and sparkly striped cardigan. Still, the pieces aren’t enough to rekindle old love—at the party, Serena walks in on Dan kissing Blair. 

Though she’s initially resistant to Dan and Blair dating, Serena gives her blessing in episode sixteen. By then, she has other things to worry about: When CeCe dies, her family finally discovers that Charlie is Ivy and that Carol’s real daughter, Lola, also lives in the city. Not only that, but Georgina has passed Gossip Girl’s laptop to Serena, encouragement to take over the site rather than waste her time on her flailing Spectator blog.

These two stories intersect when Serena uses Gossip Girl to divert attention from herself and anoint Lola as the “new Serena” (5.19). As Blair reminds her friend, the first Gossip Girl post was Serena in a wet white dress: “You didn’t really become Serena van der Woodsen until you got naked on that aircraft carrier. . . . A photo landed on Gossip Girl and that was it.” Never mind that Serena was fourteen at the time, never mind that she never consented to the post—Serena decides to use the same weapon with Lola, taking her to Kiki de Montparnasse for gifted lingerie. While her cousin tries on the “Serena” slip, Serena pulls the fire alarm and escorts her to the street.

Her plot backfires: Kiki asks Lola to model alongside Serena, then renames the slip from “Serena” to “Lola.” Suddenly, Serena feels her it girl status slipping away, and she writes another post saying Lola staged the slip photo. “Doesn’t she realize that there can only be one it girl on the Upper East Side? And that will always be Serena van der Woodsen.”

Indeed, Lola takes attention from Serena in every way—not just from the public but from her father. In episode twenty-one, Serena sees William having lunch with Lola; guess what, he’s Lola’s long-lost father. “All you ever did was avoid me,” Serena tells him later, “and then now when you find out about Lola, you just rush to be by her side.”

Serena has no interest in being a sister to Lola; she just keeps falling deeper and deeper into Gossip Girl land—until an intervention from Lola and Nate returns the laptop to its original owner. She slowly starts to get her “life and friends back”—but then Gossip Girl drops a post in episode twenty-three, a scan of one of Blair’s diary pages. Serena took the scans back when she was running the site, and now the original GG is using them against her.

In the finale, Serena is back to the color palette she wore at the beginning of the season, her first outfit an orange halter top, blue floral skirt, and beaded necklace. She’s received an invitation from David O. Russell to the Beautiful and Damned premiere—a chance to get back into the industry she loves. Blair, however, is furious over the diary posts; as revenge, she writes a fake one saying that Serena never read The Beautiful and Damned, and once it’s posted, Russell rescinds Serena’s invite.

After Blair kicks her out, Serena takes her own revenge: at the Shepherd divorce party (a nice tieback to the Shepherd wedding), she gets Dan drunk and spills cocktails on him. When they go to the bar to dry off, she convinces him that Blair has chosen Chuck, and they sleep together. After, Dan discovers that her phone camera was recording them and realizes she manipulated him into sex—neither the show nor Serena herself understanding what a huge violation of consent this is.

Serena’s dress is not gold (as it was the night she slept with Nate) or even yellow. No, she’s wearing bright blue, the same shade she wore to graduation, the day Gossip Girl labeled her “irrelevant.” Serena is still terrified of becoming irrelevant—to Gossip Girl, yes, but also to Dan, the person who once crafted a whole mythology around her. When Dan tells he doesn’t “know who [she is] anymore,” she’s devastated.

She takes one last shot at him, stopping by the loft in a coral trench, striped shirt, and sparkly skirt. She says she deleted the video, that there’s “nothing standing in the way of [them]” anymore. Dan, unsurprisingly, never wants to see her again.

Serena ends up on a train out of Grand Central, an inverse of her return in the pilot. This time, Damien’s fellow dealer joins her, handing over the little white baggie she requested. He starts to kiss her neck, tells her his name is Zeke. “I don’t care what your name is,” she replies, staring out the window.

Serena’s outfit, too, calls back to the pilot, a striped shirt in both scenes. The other components, however, are different—her coat bright coral instead of a muted brown, her bottoms a sparkly skirt instead of dark-wash jeans. She’s no longer interested in showing her friends and family she’s changed; there’s nowhere she’s headed, no one she’s going back to.

Season Six

Blair, Chuck, Nate, Dan, and Georgina spend the premiere searching for Serena—the latter two hoping to find an ending to Dan’s scathing new exposé, Inside Out. No one’s heard from Serena all summer, and the viewer’s only glimpse is a shot of her passed out on the train, her nose bleeding. They find “Sabrina” instead, hosting a wedding at her new boyfriend Steven Spence’s house in Poughkeepsie. Serena has given him her character’s name, her birthplace as Wisconsin, her alma mater as Vassar. As she tells Blair, she began the summer being revived by paramedics; she wants a “fresh start” with Steven—away from the city, away from her family and former friends. Even her dress is a shadow of who she once was—the palest yellow and white, trimmed with lace.

By episode two, however, she’s back in the city with Steven. He’s an older businessman, the wealthy owner of a “holistic health company,” with the power and influence to get her on the Central Park Conservancy board. Philanthropy is a new path for Serena, the one her own mother and grandmother took when they got a little older, a little less “wild.” Indeed, her entire wardrobe around Steven has taken on a more conservative, Lily-like tone: a pair of statement earrings or a statement necklace matched with a simple solid or printed day dress (the neckline perhaps a little lower or the fit a little tighter than Lily would choose, but similar all the same).

When Serena suspects Steven is cheating on her (and with Nate’s new love interest, no less), she tells Lily, who advises her not to make a scene at the conservancy gala. “Tonight is your entrée into adult society,” Lily reminds. “That’s the difference between being a grown-up and in high school.”

But guess who is in high school? Nate’s new love interest (yuck)—and Steven’s daughter. Yes, Steven hasn’t yet told Serena that he has a seventeen-year-old daughter named Sage. Even more disturbing, Sage acts and dresses quite a bit like the rebellious old Serena, giving even more meaning to Serena’s new maternal style.

Like Serena, Sage attends Constance, and like Serena, she pairs her uniform tie and skirt with a white T-shirt and layered necklaces, her minions imitating her in white tees and denim vests or moto jackets. They look as if Serena reigned at Constance, a little dash of Blair from their hats as headbands.

It’s decidedly creepy, Steven dating a slightly older version of his own daughter, and in episode four, the story becomes even more twisted. After Steven discovers that Serena and Nate once dated, they decide to share their sexual histories—Serena lying and saying the last man she slept with was Ben. Again, she’s dressed like Lily in an orange sheath and statement earrings, the scene reminiscent of the time Rufus and Lily made lists of their sex partners (2.19). One name on Lily’s list? Steven Spence. They slept together while Serena was still in grade school, Steven so wasted on alcohol and painkillers that he doesn’t remember until Lily reminds him.

Serena, unsurprisingly, is disturbed by the idea of sharing a partner with her mother, but Steven asks her to try to forget about it. She attempts to, both in memory and wardrobe. By the next episode, she’s done away with the Lily drag, dressing in a navy top with arm cutouts and a pink printed skirt. Steven is acting strangely, almost forgetting to invite her to Sage’s cotillion, and with a peep at the ring box in his briefcase, she finds out why: he’s planning to propose. He asks Lily for her permission, but with a little prompting from Blair, she says no.

“I knew you wanted someone,” Lily tells her daughter. “But let’s face it, Serena. You don’t have boyfriends, you have life rafts.” Lily takes her life rafts, Serena counters, and leaves her “to drown,” her primary example being marrying Rufus and making it impossible for her to date Dan.

Unfortunately for Serena, Sage also knows about her father’s proposal plan, and she’s obtained a copy of Dan and Serena’s sex tape. (Yeah, Serena didn’t delete it last season.) As Sage is presented at cotillion, the tape plays on all the screens. Blair is furious, likening the act to taking “Nate’s virginity on that bar when [she] still loved him.” Steven, too, is angry at Serena for lying and breaks up with her.

At the end of the night, all who’s left is Dan, bobbing through the water like the last life raft. He asks if she’s okay and takes her out for a burger, his bow tie, black shirt, and vest reminiscent of the night they attended cotillion together. Serena, however, looks nothing like that night, no gold in sight. She’s wearing a strapless navy and black-beaded gown, black statement earrings. Perhaps her gold gown was too tainted with memories of Ivy, perhaps she was trying to be more mature, stately—like Lily. Either way, the effect is strangely mournful, fresh from the loss of Blair and Steven; sparkling, just a little, at the possibility of Dan.

In episode six, Dan and Serena are friends again, Dan staying in Eric’s old room. Serena’s style has veered to season one or two: a chunky necklace, red cardigan, black top, gray skinny pants, and boots. Indeed, the entire episode is packed with season one and two Derena tropes: Vespas, pool, chocolate-covered strawberries, stuck elevators. While Serena can’t quite reconcile the Dan in front of her with the Dan who’s been publishing scathing chapters about his friends and family, she also can’t quite let go of the idea of being his perfect Serena again. “I feel like I did when I first came back to the city from boarding school,” she tells him before he kisses her, “when all I wanted was a fresh start.” But the thing is, Serena is always looking for a fresh start—with Steven, with Dan, with Ben. She just keeps running into herself, her past. 

Serena and Dan begin dating, having made up with their friends. They even invite them all to Thanksgiving at the penthouse (6.8). In the middle of dinner, Dan’s Serena chapter finally publishes: “Golden Girl Falls from Grace: A Faux Love Story.”

Serena is devastated by Dan’s dissection of her, even reads the following paragraph out loud to him:

Serena is nothing. She’s a golden shell. Give her love, and she’ll do anything you want. With daddy issues like these, it’s not hard to push the right buttons, and once you do, the most powerful girl on the Upper East Side has no power at all.

By the following episode, she’s decided to move back to California, to finally escape her past. “In Los Angeles,” she tells Blair, “nobody cares if I date the wrong guy. . . . I have the chance to reinvent myself.” She almost makes it, too, until she finds a chapter tucked in her plane reading: the other Serena chapter, the good Serena chapter.

Serena goes to Dan’s apartment, demands to know which chapter is real. Dan explains through flashback, a long-awaited look at that party where they first met.

Interestingly, flashback Serena is not too different from present-day Serena: she wears a multistrand necklace, sequined tank, and black cardigan; present-day Serena in a tweed jacket, dress, and similar multistrand necklace. Remember, too, that this is drunk-Thanksgiving era Serena—the Serena in a short green dress and leopard coat. It seems strange that flashback Serena would look so put-together, as if Dan is placing a contemporary lens over his memory.

He looks up at her as she stands at the top of the Waldorf staircase—as he did on their first date, as he did before Blair’s wedding. Always looking up at her, his fantasy, his inspiration for Gossip Girl. Serena is fine with Dan being Gossip Girl, even going so far as to call the blog a “love letter.” She would see it that way; after years of being brought to her highest highs and lowest lows by Dan’s writing, she finally has a work to point to that says she was the definitive center, the muse for it all.

Five years later, Dan and Serena marry, Serena finally descending the stairs, still encased in her golden shell—this time, the gold bodice of her wedding gown. She looks beautiful, happy, but says nothing. Blair and Jenny get a few lines, hints at their careers in fashion design; we even learn what Lola is up to. But Serena? Nothing, nothing about her work, her life—only her relationship with Dan.

I wish, sometimes, that the writers had let Serena stay on that plane. That five years ahead, she’s writing her own narrative—producing movies in Los Angeles or traveling the world. Instead, her shell is empty—free from her past and free from any future, too.

[Stay tuned for Chuck Bass’s profile on Thursday, 5/13.]

DP on GG

My partner, Daniel, spent 2020 overhearing episodes of Gossip Girl from various rooms of our apartment. He still doesn’t understand the show and he doesn’t care.

DP: (hearing William van der Woodsen) Is that a Baldwin brother?

CL: Yes.

DP: Steven?

CL: No, Billy, I think?