The Revision of Dan Humphrey

Originally published on Substack 3/11/2021

[This profile contains discussion of sexual assault.]

Even if you haven’t watched Gossip Girl, you probably know that Dan Humphrey is the titular blogger. His identity was revealed in the series finale, the revelation followed by memes and Tumblrs and listicles, all trying to answer the same question: How could Dan possibly be Gossip Girl? And if he is, is he a sociopath? This profile presents me with a similar question: How do I deal with the Gossip Girl of it all? Do I analyze Dan’s costume design, from season one to just before the finale, assuming that he is indeed Gossip Girl and is dressing as such? Or do I interpret his style up until the finale as plain ol’ Dan Humphrey’s, then execute the most dizzying 180-degree turn in the history of this newsletter? 

Somewhere in between, I think.

Some backstory: As I discussed in my introduction, I was a Dair (Dan/Blair Waldorf) shipper back in seasons four and five, then stopped watching after the show turned back to Chair (Chuck Bass/Blair) in the season five finale. (We’ll discuss the latter relationship in greater detail in my Chuck and Blair profiles.) Of all the show’s shipping wars, Dair vs. Chair was the most passionate, the most vicious, and ultimately, the show went with the pairing that had longer history and more fans. To quote every Dair fan ever:

How do shipping wars connect to Gossip Girl’s identity? Well, here’s my theory: the show did not settle on Dan until season six. My evidence: The showrunners considered Eric van der Woodsen and Nate Archibald first, and, according to executive producer Joshua Safran, did not commit to Dan as Gossip Girl until Safran had already left the show. His last episode? The season five finale, “The Return of the Ring.” Dan’s season six arc must’ve been written to retroactively make sense of his identity as Gossip Girl—not only to facilitate a happy ending for Chuck and Blair (and eliminate any likelihood of a Dan and Blair reunion) but also to rekindle the romantic relationship between Dan and his on-and-off girlfriend and muse, Serena van der Woodsen.

All this is to say that I’m not going to spend seasons one through five writing, “Dan is wearing a shirt with little O’s on it, he’s Gossip Girl XOXO!!!” Rather, I think it’s likely that the costume designer, Eric Daman, was told Dan was Gossip Girl sometime during season six filming, and so I’ll proceed with season six through the lens of Dan as his alter ego. Until then, Dan is Dan, or, as he supposedly deemed himself, “Lonely Boy.”

In seasons one and two—aka the high school years—Dan’s costume design is defined by both his outsider status as a partial-scholarship kid from Williamsburg and his academic and writerly aspirations. In the season five extra “5 Years of Iconic Style,” producer Stephanie Savage describes his style as “kind of a hipster but also having this sort of academic quality to him.”

Dan’s wardrobe staples reflect the melding of these two identities. He often wears the same pieces with his school uniform: a military-style cargo jacket (one I’ve always imagined he bought from an army/navy surplus store) and a tan satchel. When he’s out of school, he chooses vests, button-downs, cardigans, skinny ties, often in earth tones or plaids, to match his father and sister, Rufus and Jenny. The biggest brand name Dan wears is L.L.Bean.

His actor, Penn Badgley, sings Daman’s praises in the season one extra “Gossip Girl Couture”:

Dan’s style greatly benefits from Eric being our costume designer, because otherwise he’d probably be like in khakis and, you know, Doc Martens. . . . He wears skinny jeans, a lot of button-downs with the sleeves rolled up, cardigans over it, nice jackets, great shoes, nice, like, Italian loafers. . . . On another show, the same character would not look at all the same.

Indeed, in the same video, Daman describes Dan’s early style as “vintage-feeling, like sixties kind of French New Wave [shirts] and really great beat-up dress shoes . . . kinda dressed up because we don’t want him to look like some schlocky Williamsburg guy” (“Couture”). As much as Dan judges his wealthy Upper East Side classmates, he also wants to fit in with them—with his new girlfriend, Serena—and so he dresses, to quote Daman, “as appropriately as he can within his means but still [keeps] his own personal style” (“Couture”).

As the seasons go on and Dan finds greater acceptance at NYU and further entrenchment in the UES world, his style became more predictable, more typical: for day, medium-wash jeans paired with a plaid flannel or solid Henley, sweater, or T-shirt, usually in gray, brown, dark red, or navy; for night, a black suit and tie with a white button-down. That is, until season six, when his style pivots in small but unexpected ways—signaling, perhaps, to the viewers the revelation to come.

For what it’s worth, Daman loved the finale reveal. He told Fashionista:

I love that Dan is Gossip Girl. I do! It was an unexpected turn. He, through all six seasons, was so holier than thou, judging all those kids, but then you realize he just felt ostracized and wanted to be a part of it in such a big way that he had to take this on. Then it just consumed him and he became Gossip Girl. I think it was a great choice. Like who was it going to be—Georgina?! [Laughs]

Oh, I wish, Eric. I wish.

Season One

The show opens at Grand Central: Serena returning from boarding school, and Dan and Jenny returning from a visit with their mother in Hudson. Dan and Jenny are greeted by their father, Rufus, but there’s no one to welcome Serena home except Melanie91, who takes a photo of Serena and sends it to Gossip Girl. Dan spots Serena from across the concourse, stunned by the sudden reappearance of his secret crush, who’s been away for a year. He wears a brown jacket with a corduroy collar, striped sweater, plaid shirt, and jeans. The browns match Rufus and Jenny but also Serena: she, too, is wearing a brown coat with a striped top. 

Gossip Girl posts Melanie91’s photo, mentioning, for the first time, “Lonely Boy” and his crush on Serena.

The first school day after Serena’s return, Dan wears the usual St. Jude’s uniform: navy blazer, yellow button-down, red-and-yellow striped tie, and khakis. Unlike his Upper East Side male classmates, who wear preppy trenches or peacoats and leather bags, Dan pairs his uniform with the aforementioned cargo jacket and satchel. Even his haircut is military-like: a buzz cut, severe and rule following, much like Dan himself. The satchel is made of tan canvas: a cheap, functional fabric that matches his khakis.

Though he’s spoken to Serena only once—at a freshman-year birthday party—he decides to visit her at the Palace. They bump into each other and she leaves her phone behind, giving him reason to return the following morning and stumble into a date with her.

He takes her to a concert—his dad’s band, Lincoln Hawk. His date look, like his first outfit, is influenced by both Serena and the Humphreys: a tweed vest (not unlike the gray one Serena was wearing under her coat at Grand Central), striped button-down, striped scarf, and plaid coat. Dan and Serena end up at the Kiss on the Lips party, rescuing Jenny from Chuck.

In episode two, Dan visits the Palace again; this time, Serena brings him to the Bass fundraiser brunch. He’s unprepared for the event, his striped shirt, brown military-style jacket, and jeans woefully underdressed alongside Chuck’s and Nate’s suits. His Serena-inspired stripes aren’t enough to save him from the Humphrey moral rigidity of his brown coat. Once Blair tells him why Serena fled the city—Serena slept with Blair’s boyfriend, Nate, at the Shepherd wedding—Dan goes back to Brooklyn, his perfect image of Serena shattered. As he tells his family later, “Turns out [Serena’s world] wasn’t for me.”

Serena’s world, too, is his Upper East Side prep school; she attends the sister school, Constance Billard. Despite his academic excellence, Dan struggles to distinguish himself among his more privileged classmates. He interviews to be the usher for the Dartmouth rep at the schools’ Ivy League mixer (1.3), but the position goes to Nate instead—the kid may have poor grades, but he’s a Dartmouth legacy. Dan is stuck doling out refreshments, the first instance in a motif—Dan serving his wealthier peers.

At the mixer, Serena saves her brother, Eric, from a public revelation. Her selfless sacrifice and familial loyalty restore her in Dan’s eyes, and they make up. “Obviously I don’t know anything about your life,” he tells her.

Two episodes later, they go on their first official date. Though he claims to know nothing about Serena’s life, Dan attempts to emulate it for their date, emptying his piggy bank to hire a driver and pay for a fancy dinner. Serena—bored by the trappings of the Upper East Side—expects Vespas and Brooklyn galleries, and in the end, they play pool at a dive bar. For the first half of their date, Dan goes formal, or at least formal for Dan: a paisley-print shirt, brown tie, and brown suit. But, as the date goes on and he loosens up, he takes off his jacket, rolls up his shirtsleeves.

In episode six, Dan’s childhood friend and crush, Vanessa Abrams, returns. In their first scene together, he wears a striped button-down and gray argyle cardigan—Vanessa may have feelings for him, but his heart is already claimed by Serena. Their relationship is becoming more physical: they make out at school, Dan in his usual coat, Serena in Dan’s argyle cardigan. Serena has had sex before, but Dan hasn’t, and so this cardigan becomes a symbol of their growing sexual intimacy, passed back and forth like saliva. As noted in Vanessa’s profile, Serena is even wearing it the morning after they almost sleep together for the first time.

In episode ten, Serena’s grandmother, CeCe, arrives—to Serena, she’s a charming free spirit; to Dan, a calculating fake. CeCe wants Serena to attend cotillion—a tradition Dan vocally opposes—so she manipulates her daughter, Lily, with her cancer diagnosis. CeCe chooses an Upper East Sider, Carter Baizen, for Serena’s escort and tells Dan to give up—he’ll never fit in, and Serena will end up with someone like Carter. When Serena approaches, asking what they’re talking about, Dan tells her that CeCe has agreed to him as her escort.

For this scene, Dan wears a striped gray-and-black cardigan over a white button-down and skinny black tie—the stripes, of course, are for Serena, but the simple shirt and tie pairing will appear again and again, often when Dan is in a position of servitude. He may have outwitted CeCe once, but that doesn’t mean he will again.

For the cotillion itself, Dan chooses a black suit, dark gray shirt, and black bowtie. The back of his vest is gold, to match Serena’s gown, but covered by his jacket when he arrives to escort her. He tells Serena about CeCe’s manipulations, but she doesn’t believe him, and they agree not to attend together. Later, once Serena realizes that Dan is right, they reunite. This time, Dan’s jacket is off, revealing the gold vest that ties him to his date.

In the next episode, Vanessa gets Dan the best Christmas gift—publication of his short story in The New Yorker—and Serena wants to buy him something equally wonderful. First, she gives him a fancy watch, which Dan refuses, citing his most expensive Christmas present as a pair of L.L.Bean boots. They agree to a price limit of $50: Dan gets her a Christmas tree for her rooms at the Palace, and Serena gets him snow, in the form of a video installation. There, surrounded by fake snow, Dan shares his short story with Serena, a recollection of their brief exchange at that fated freshman birthday party. Those few sentences—and, I have to imagine, Serena’s charisma and blond beauty—were enough to sustain Dan for two years. That night, he and Serena have sex for the first time.

For most of this episode, Dan wears a brown cardigan, polka-dot shirt, and jeans—but most important, his brown corduroy-collared jacket on top. He first wore this jacket in the pilot, when he saw Serena at Grand Central, and in many ways, this episode is a culmination of his obsessive crush—and his first Gossip Girl mention. His romanticized version of their meeting finally “got” the girl.

Their happiness, however, is short-lived: there’s another reason Serena left the city for boarding school, and only Serena’s old friend Georgina Sparks knows it. Georgina returns in episode fifteen, wanting to pick up their party-girl ways. After two drunk, drugged nights with Georgina—and multiple lies to Dan—Serena tells her she doesn’t want to see her anymore. Dan never knew the “old Serena,” and Georgina and Serena’s secret could break the pedestal he puts her on.

Georgina does not take Serena’s rejection well, and she decides to infiltrate her friend’s world through a different route—by introducing herself to Dan as “Sarah,” just a wide-eyed girl trying to make friends in the big city! When Dan meets “Sarah,” he’s wearing a plaid button-down and a tan cargo jacket (1.15)—not unlike the brown version he wore to the Bass brunch, the day he learned the other reason Serena left New York. The silhouette reminds us of the first time Dan judged Serena for her past and hints that he’ll do the same for this secret.

(The secret, to be honest, is not worth all this hiding: Serena believes she killed someone, when she only encouraged him to do a line of cocaine that led to his fatal overdose.)

After hearing plenty about Dan’s new friend, Serena finally meets “Sarah”—who, of course, blackmails Serena into playing along with her new identity. Not wanting to reveal her secret, Serena continues lying to Dan, ultimately telling him that she cheated on him. He’s devastated and breaks up with her (1.17).

Later that day, he attends a Lincoln Hawk concert with “Sarah” and Vanessa. There, a concertgoer calls “Sarah” by her real name, and Dan asks her why. Georgina cries and offers a quick yet effective lie: she changed her name to escape an abusive ex-boyfriend. Dan can never resist a “damsel in distress” story, and so they go back to the Humphrey loft together, all before Serena can find him and tell him why she lied.

At the concert, Dan repeats a brown varsity jacket with a black button-down. As discussed in my Vanessa profile, Dan first wears this jacket during the pool party episode (1.12)—another time when he was on the outside of a big Upper East Side secret.

In the season finale, Dan finally hears Serena’s story and helps run Georgina out of town, but the couple’s eventual candor is not enough to repair their relationship. At a wedding, they break up for good: Serena in a yellow floral bridesmaid gown with black accents; Dan in a black suit and tie and muted yellow shirt. The pair match but barely: Dan distressed by Serena’s dishonesty (“You lied to me over and over and it was easy for you”), and Serena shattered by Dan’s judgment (“I’m not who you thought I was and you can’t forgive that”). They begin the summer separately—Dan interning with a famous author, Jeremiah Harris, and Serena relaxing at her grandmother’s house in the Hamptons.

Season Two

In the season premiere, Dan is fired from his internship; he was supposed to complete a short story, but he hasn’t been inspired since he and Serena broke up. She was his muse, the golden girl onto which he projected all of his hopes and fantasies, but this past year devastated that image. She’s no longer the girl he wrote his New Yorker story about.

Dan goes out to the Hamptons to find his muse, who’s attending the White Party. CeCe lends him her dead husband’s off-white “suit from the seventies,” which is actually kind of perfect for Dan: not in style but vintage; a little frumpy, wrinkled, and hipster alongside the crisp whites of the Hamptons set. He and Serena reunite on the beach and then spend the next two episodes trying to decide if they’re dating again.

At the beginning of episode three, they’re back in the city, getting gelato together, Dan in the same striped T-shirt from the brunch episode. The shirt echoes Serena’s striped tank but also hints at their troubles to come, the same troubles that have been haunting them since episode 1.2. They haven’t resolved the issues that led to their finale breakup, so they’re fated to break up again, this time in a stalled elevator.

Dan is outfitted in a striped shirt and suit, Serena a honeycomb-print dress with a Chanel logo belt—similar color palettes, like at the wedding, but completely different worlds. Dan buys cheap thrift and vintage, while Serena buys expensive designer, the interlocking C’s prominent at her waist.

On the first day of senior year (2.4), Dan wears his usual uniform and makes flirtatious friends with a new student, Amanda. She’s basically the female Dan: a blue button-down and tie, a little tweed vest, and a copy of Jeremiah Harris’s book. Serena, distressed by the idea of Dan dating someone new so quickly, suggests all three hang out together.

To their date, Dan chooses essentially the same pieces Amanda wore to their first meeting—a button-down and vest—while Amanda wears a plaid tube dress, her fashion again tying her to Dan. Serena is out of place in a bandage dress, out of depth as Dan and Amanda discuss books. As we learn later that episode, Chuck hired Amanda to flirt with Dan, a move that Chuck hoped would push Serena to become Constance’s new queen bee. Suddenly, Amanda’s clothing choices make sense; you can imagine Chuck, the most fashion-conscious man on the show, encouraging her to wear vests and plaid as some sort of mating call.

By the next episode, Dan has found a crotchety old mentor, author Noah Shapiro, to write him a recommendation letter for Yale. Shapiro tells Dan to break out of his rut, to write something other than his usual sadboi stories. Dan picks a new muse—Chuck—and goes on a drunken, drugged adventure with him. The next night, Chuck finds the story Dan’s writing about “Charlie Trout,” but not before revealing his most closely kept secret: his mother died giving birth to him, and his father, Bart, hates him for it. 

In this scene, Dan wears a pale pink button-down—an unusual color choice for him, much more Chuck-like. He’s softened by Chuck’s revelation and decides not to use him for his story.

That is, until a few episodes later (2.9): driven by his sister’s newfound fame in the fashion world, Dan decides he cannot wait for his own success and sends a new Charlie Trout story to Shapiro. Rufus advises him against it: “Success, people praising you, that goes away,” says Rufus. “And if you don’t like who you are, you’re done.”  A lesson, I think, Dan would be well to remember in the coming seasons.

In the next episode, a New York magazine editor offers Dan (a high school student, remember?) an exposé on Bart Bass. Dan accepts and tells Bart that he wants to shadow him a few days a week. He does so in a black blazer, a black shirt—quite literally, a shadow. After he learns a secret that could devastate Bass Industries, he kills the profile on Rufus’s advice, not wanting to destroy the Bass family (and, consequently, Bart Bass’s stepdaughter, Serena).

The next handful of episodes are consumed with Dan and Serena’s romantic reunion and the disclosure that they share a half-sibling—the revelation, surprisingly, does not instantly turn them both to dust.

Episode sixteen marks the first appearance of Miss Rachel Carr, a new teacher at Constance. Serena loves Miss Carr, the first teacher to take her seriously, and introduces her to Dan. Unlike the Amanda decoy earlier this season, Miss Carr is truly a female Dan: obsessed with literature and academic neutrals. In her first scene, she wears a black cardigan, gray T-shirt, and gray plaid skirt.

Miss Carr recently moved from Iowa, and Dan encourages her to explore the city, maybe stop by his father’s art gallery in Brooklyn. She does so at the end of the episode, the beginning of their inappropriate friendship.

Blair, desperate to get back at Miss Carr for a poor grade, spreads a rumor that Miss Carr is sleeping with Dan (2.17). She isn’t (yet), but Miss Carr is dense enough to go to coffee with Dan later that day. Serena sees them at the restaurant, Dan comforting her teacher, and takes a photo—evidence that is soon used to fire Miss Carr. Their outfits alone say they’re about to become even more intimate: Dan in a navy sweater, Miss Carr in a gray argyle sweater. Remember that gray argyle cardigan that Dan and Serena traded in season one? It’s about to show up again.

After Miss Carr’s firing, Serena and Dan break up, and he goes to Miss Carr’s apartment to apologize. They have sex, Miss Carr deeming it morally and consensually okay now that she no longer works at Constance. Little does she know, the headmistress has just decided to reinstate her as a teacher, citing insufficient evidence for their relationship.

In episode eighteen, Miss Carr is back at school, the Constance and St. Jude’s students uniting for a production of The Age of Innocence. She and Dan end up having sex in the costume closet, Rachel in a white tank with a visible bra (a symbol, I think, of how unprofessional she’s become) and a gray. Argyle. Cardigan. Does Dan give a cardigan to every woman he has relations with?

Dan himself is in white tie, his Newland Archer costume, and so he paraphrases the words and gestures of the character: “You know this can’t last,” he says. “Our staying away from each other.” As Miss Carr tears up, he kisses her wrist, just like Archer kisses Countess Olenska’s wrist. Writerly Dan can’t help but to romanticize this woman through literature, to damsel her distress, all while she engages in an incredibly inappropriate and illegal relationship with him. Dan soon learns that Miss Carr intentionally ruined Blair’s admission to Yale, and Miss Carr, guilt ridden over her choices, goes back to Iowa by the end of the episode.

Dan has gotten into his own dream college, Yale, but his family hasn’t received enough financial aid. Wanting to contribute, Dan takes a job as a cater waiter behind his father’s back, his first gig at the Waldorfs’ Passover Seder (2.21). Of course, Rufus and Lily are invited, and Dan must pretend that he’s there as a guest, not an employee. Lucky for Dan, his cater waiter uniform is in-line with his style: black pants and vest, a white button-down, and a skinny black tie (“a classic look,” to quote him and Rufus). In fact, prior to this episode (see, for example, the outfit he wears when he manipulates CeCe) and throughout the rest of the series, Dan often wears a white button-down paired with a black tie and vest or jacket for formal events. It’s just proper enough to fit in, but not quite enough not to convince his wealthier counterparts that he’s one of them and not there to serve.

Dan gives up Yale for NYU—the least believable plotline of the series. Sure, he’ll save on housing, but I seriously doubt that NYU offers better financial aid than Yale. Go to Hunter, Dan! Or Brooklyn College! They have good creative writing programs! Oh my god.

In the finale, Dan and his classmates graduate. During the ceremony, a Gossip Girl blast bestows a “diploma” on each of the main characters; Dan is “the ultimate insider,” Serena “irrelevant.” Shaken, Serena decides to uncover Gossip Girl’s identity and invites her to a bar that night. Instead, Gossip Girl texts all the characters, telling them to meet her there. 

Dan arrives first, wearing a plaid shirt and a vest, much like in the early days of his relationship with Serena. “Gossip Girl might be right about me,” he tells her, “but she’s wrong about you. Without Serena van der Woodsen, who would I have dreamt about? I might have spent my whole life on the outside if you hadn’t let me in.” Despite all his judgment of the Upper East Siders, Dan is happy to be let in, to be listed among them.

Season Three

After all, his father is about to marry Lily, to move their family to her Upper East Side penthouse. The Humphreys spend the summer at CeCe’s home in the Hamptons, Dan’s first appearance of the season in a short-sleeved button-down and Ray-Bans—not the priciest sunglasses in the world but certainly more expensive than any high school Dan would’ve worn. Almost all the signifiers of Dan’s newfound proximity to wealth are fashion items: A leather wallet full of crisp hundreds—a graduation gift from Lily. A tan suit for a polo match—a present from CeCe, essentially an upgrade of the seventies suit he wore last season.

There’s certainly more of an ease to Dan this season: he’s finally Upper East Side by marriage, and yet he’s more popular than he’s ever been for being himself. On his first day at NYU, a fellow student compliments his New Yorker short story and invites him to her writers’ group. Even fellow freshman Blair senses his cachet and asks him to escort her to Georgina’s party. Georgina says she wants a fresh start, but she really enrolled at NYU to take revenge on Blair. When Blair tries to embarrass Georgina, Dan can’t resist another damsel and comes to her defense; that night, they rekindle the attraction that sparked in season one.

Dan and Georgina keep things casual for an episode or two, Dan eventually breaking things off to pursue Olivia Burke, a new NYU student and undercover movie star. Not only is Dan cool at NYU but he’s dating-a-movie-star cool. Gone are the vintage button-downs and military coats of seasons one and two, replaced by jeans and simpler, more modern tops: plaid shirts and Henleys and sweatshirts. It seems Dan no longer needs his clothes to say, “I’m different,” “I’m interesting,” “I’m smart”—at NYU, it’s just assumed he is.

When Olivia must leave NYU for a movie role, Dan and Vanessa take her through a college bucket list. The last item, completed at the end of this drunken night, is a threesome. The reality and recollection of this threesome, of course, are two different things. In reality (3.9), Dan wears a plain tan sweater, but in his recollection (3.10), Vanessa and Olivia simultaneously unbutton and open a blue plaid shirt. Two women undoing your button-down is certainly a sexier image than them pulling a sweater over your head—not only that, but Dan’s fantasy outfit shows that his self-image is in plaid.

Dan and Olivia soon break up, Olivia having realized that Dan has feelings for Vanessa. A few episodes later, Dan and Vanessa begin dating after kissing at a beach-themed party, Dan in a gray tank top and swimsuit. From there, he continues his parade of flannels and Henleys until episode eighteen, when he attends a pre-wedding party at the Waldorf penthouse. The family’s longtime maid, Dorota, is the bride.

Despite being a guest at the event, Dan refills the ice bucket at Eleanor Waldorf’s request. Naturally, Dan is dressed like a cater waiter for this scene: black suit and tie, a light-colored shirt, all calling back to when he worked the Waldorf Seder. He may have moved away from the vests that he favored in the first two seasons, but he can’t fully escape the impression that he’s there to serve.

Dan and Vanessa continue to date, though she accepts a summer internship in Haiti in episode twenty. She’s barely gone when Dan wakes up in bed with Serena, having spend the night drinking and talking and, yes, kissing.

In this scene, Dan wears a similar tank top to the one he wore to the beach party earlier this season, a sad reminder of the moment that began Dan and Vanessa’s relationship. Once Vanessa sees a photo of Dan and Serena on Gossip Girl, she refuses to talk to him. He plans to follow Serena on her summer trip to Paris, but just when he’s about to buy a ticket, Georgina shows up—pregnant, she claims, with his baby.

Dan’s blue plaid shirt matches Georgina’s top—blue sequined, much like the dress she wore when they first hooked up at her party. Even in fashion, you reap what you sow.

Season Four

Dan spends the summer living with Georgina at the loft and avoiding his friends and family. Only once Vanessa checks in (4.1) is his secret discovered: Dan has a son named Milo, dressed like a Humphrey in brown tones. Thanks to a bit of manipulation from Nate and his new girlfriend, Juliet, Dan and Vanessa get back together, Vanessa helping with Milo once Georgina leaves suddenly. When Georgina returns (4.3), she reveals that Milo isn’t Dan’s son—she was using Dan as a decoy to escape the birth father’s vengeful wife.

In the next episode, Dan is in denial, ignoring the deep pain he feels at the sudden loss of Milo. Vanessa attempts an intervention, but Dan leaves to hang out with Serena—the perfect person to help him avoid, to numb rather than confront. They’re even dressed in similar colors and fabrics—Dan in a chambray shirt, Serena in a denim blazer and striped mini. Later, he realizes Vanessa is right and takes time to grieve.

Still, Dan and Vanessa aren’t long for this season, breaking up over Vanessa’s jealousy of Serena (4.5). For every woman Dan dates, Serena is always a golden specter, his beautiful first girlfriend, the one he can’t let go of. Not long after the breakup, Dan and Nate compete for Serena’s affections at the masked Saints and Sinners party (4.9). Little do they know, they’ve been set up by Jenny, Juliet, and Vanessa; when they’re both kissed by Serena, she’s actually Juliet in disguise.

Serena herself chose the light gray-blue gown for the event—a saint, much like Dan in his light gray suit. She was planning to pick Dan and would have if she hadn’t first been foiled. Unbeknownst to Jenny and Vanessa, Juliet drugs Serena and dumps her at a Queens motel—there she wakes up a few days later, remembering little of what happened.

Only Dan believes that Serena hasn’t returned to her partying ways—as Blair points out, he is the most recent addition, the only one of her friends who got to know Serena after she returned from boarding school. To visit Serena at her rehab center, he wears an olive-green Henley and leather jacket, the color of his shirt perfectly matching her sweater—a sign of his faith in her. By the end of the episode, Blair has learned that Juliet is responsible for Serena’s state, and she and Dan unite to take her down.

Thus begins a string of outfits that warm my shriveled Dair heart: Dan and Blair in beautifully coordinated gray and plaid; Dan and Blair in matching red plaid. In their time hunting down Juliet, Dan and Blair realize that they’re more alike than they thought: they share the same taste in films, the same love for museums. They could almost—dare they say it?—be friends.

They’re a strange pairing, certainly—Blair represents everything Dan hates about the Upper East Side, the snobbery and the scheming. She makes fun of his style—his scarf (a gift from Vanessa), his necktie (his grandfather’s—the only Humphrey heirlooms are those born of necessity)—but he starts to laugh with her. He recognizes a drive, an eye, in her that he previously didn’t: “You’re an evil dictator of taste, Blair,” Dan says. “Why deny that just because [your mother works in fashion]?”

Inspired by Dan’s advice, Blair secures an internship at W magazine—an internship that Dan stumbles into, then leaves to allow Blair to thrive. For the next few episodes, they orbit each other, in and out of the movie theater and museum and office, usually coordinated in gray. Blair helps Dan get his article published, Dan helps Blair juggle her W responsibilities, and eventually, in episode seventeen, they kiss, both wanting to know if there’s something more to their friendship. For Dan, the kiss confirms his feelings, but for Blair, it doesn’t. Rather, the kiss makes her realize she wants to be with Chuck.

Chuck, however, knows only that they kissed, and out of jealousy, sets up Dan for humiliation (4.18): Chuck is being photographed for the Modern Royalty photo book, a who’s who of wealthy families, and arranges for Dan to be told he’s been chosen as an “up-and-comer.” Dan arrives at the shoot in a black suit and tie and a white shirt. Yet again, his cater waiter look shows he doesn’t quite belong. Chuck, in contrast, wears a black blazer embroidered with a gold crest—the ultimate sign of wealth and family legacy. When Blair learns of Chuck’s scheme, she takes Dan’s side: “Dan Humphrey may not be royalty,” she says, “but at least he’s not a child.”

But you know who is royalty? Blair’s next love interest, Louis, a prince of Monaco. His royal minder doesn’t want them seen dating, and so Blair uses Dan as her distraction. He escorts her to the Pink Party (4.19), wearing his usual dark suit and white shirt with a pink tie Blair purchased for him at Paul Smith—worried, perhaps, that he’d wear an heirloom from his grandfather.

Though Dan still harbors feelings for Blair, he distracts himself with Serena’s cousin, Charlie. After reading Gossip Girl, Charlie knows exactly what Dan wants: a damsel in distress, and more important, a damsel that looks like Serena. In episode twenty-one, they attend a St. Jude’s/Constance Billard fundraiser together, Charlie wearing Serena’s gold cotillion gown. Dan, however, is dressed in his usual cater waiter look, not the gold vest he once wore to match Serena. Charlie is only fool’s gold, their brief fling over once she asks Dan to call her “Serena” while they kiss.

The season ends with Vanessa stealing and secretly selling Dan’s novel manuscript—Dan having refused to publish it and risk ruining his Upper East Side friendships. The success that Rufus once warned of is now coming at him full speed.

Season Five

Desperate to prevent his book, Inside, from coming out, Dan goes to Blair’s now fiancé (and father of her baby), Prince Louis, to pull a Vanity Fair excerpt (4.1), and then to Chuck to uncover which publisher has the full manuscript (4.2). Finally, his former mentor, Noah Shapiro, tricks him into stepping forward by claiming the novel is his own (4.3). Even Dan will risk social rejection over another writer taking credit for his work.

In episode four, Dan hands out copies of the book to his friends and family and invites them to his book party that evening. They are, as he warns them, his inspirations, the characters cheekily renamed: Dylan Hunter, Sabrina von Sloneker, Clair Carlyle. As they read from the book, they imagine themselves in the scenes, their characters wearing the same clothes they’re wearing in real life, blurring the boundaries between Dan’s fantasy and reality. In one scene, Clair and Dylan not only kiss but furiously make out—a fantasy sequence not unlike the Jeff/Annie fan video–inspired montage from Community. In the imagined scene, Dylan wears the same dark gray suit, light gray shirt, and tie that Dan later wears to his book party. The suit is Armani, a departure from Dan’s usual workhouse black suits and white shirts—he’s not catering the party but starring in it.

Though Dan is glowingly received by his party’s literary attendees, his friends and family are furious at the license he’s taken with their lives—Serena for writing Sabrina as a shallow party girl, Blair for writing that Clair slept with Dylan. Serena is used to being Dan’s muse, and she’s shocked to find that Blair is, as Serena later admits, “the star of Dan’s book.” With Clair, he was inspired by a full person, all her good and bad, rather than a flimsy, idealized impression.

Save for his fancy suit, Dan’s season five fashion strays only a little from season four’s. His color choices, like in season four, frequently mirror Blair’s, though his shirts are more often flannels. Dan still has feelings for Blair—despite her engagement, despite her pregnancy. Blair, however, can’t quite let go of Chuck. By episode ten, Dan helps Blair and Chuck reunite, Dan in a red flannel to match Blair’s red rose–print dress. He wants her to be happy, even if it isn’t with him.

On their drive to the airport, their car hounded by Gossip Girl–tipped paparazzi, Chuck and Blair crash in Central Park. Blair loses the pregnancy, Chuck almost dies, and Gossip Girl shuts down her site, guilty over the role she played in their accident.

Believing her pleas to God saved Chuck’s life, Blair proceeds with her plans to marry Prince Louis, Dan supporting her as she tries on the Vera Wang gown she chose before her miscarriage. She can no longer wear it for her wedding, she tells him—Dan, after all, is the only other main character who has lost a child in some way and therefore can understand a small piece of the grief she’s feeling.

The scene is poignant, reminiscent of the season one scene in which Rufus accompanied Lily to her dress fitting for her wedding to Bart, and I believe the show is trying to draw parallels between the two sets of characters, both in story line and fashion. Dan, naturally, is wearing a Rufus-like blue flannel shirt; Blair’s gown shares the same shape and brand as Lily’s.

In episode thirteen, Blair and Louis marry, Dan a groomsman—a thank-you from Louis after Dan wrote his wedding vows. (Vows that, says Blair, “peered into [her] soul.”) Indeed, Dan looks more like a traditional groom than Louis—severe in his white naval uniform. Dan wears a black suit and gray vest, a pink peony boutonniere to match Blair’s bouquet.

Before the ceremony, Blair admits to Chuck that she still loves him; Dan, hoping Blair will finally call off the wedding, sends a video of the exchange to Gossip Girl—recently taken over by Georgina. Blair still marries Louis, and at the reception, he reveals that their marriage is now nothing but a contract, a business arrangement. Soon after, Blair escapes in their “Just Married” car, Dan in the driver’s seat. They spend the next episode trying to get Blair out of the country for a quickie divorce. The royal family finds her first.

By episode fifteen, the Waldorfs are attempting to arrange a divorce, and Blair is channeling her romantic frustrations into Valentine’s matchmaking, hoping to reunite Dan and Serena at Nate’s “Come as You Were” party—attendees to dress as they did in high school. Dan, naturally, wears his uniform blazer, yellow shirt, tie, and khakis, while Blair is dressed in a red gown, on her way to a gala afterward.

Blair encourages Dan to approach Serena, taking off his tie and undoing a few shirt buttons because “Serena really digs that outsider thing.” Never mind that Dan never wore his uniform like that, even when he was an outsider—Blair just wants an excuse to touch him. The fact that she’s not dressed in her own uniform only adds more nuance to their exchange—Serena may have been his high school sweetheart, but Blair is his mature love, a woman he’s grown to care for through bad and good. They kiss at the party, and with Serena’s blessing and Blair’s divorce finalized, begin dating in episode eighteen.

Their relationship thrives for a few episodes, despite others’ doubts. In episode twenty, for example, Rufus remarks on a tie Dan is wearing for an event: “It’s a Blair thing,” he tells his father. Rufus warns him not to become too subsumed by Blair’s world—just as Rufus became with Lily’s. The tie, after all, is a motif in Dan and Blair’s relationship—from the vintage one she playfully mocked to the pink one she bought at Paul Smith. It quite literally ties them, bonds them together, but it also has the potential to tighten, and to choke.

Like Rufus and Lily, Dan and Blair break up by the end of the season. Blair can’t quite stay away from Chuck, and Serena quite can’t let go of Dan. In the finale, Serena tricks Dan into thinking Blair has left him for Chuck. Drunk and heartbroken, Dan sleeps with Serena at the Shepherd divorce party, a callback to Serena sleeping with Nate at the Shepherd wedding. This time, however, Serena is secretly recording them. When Dan discovers the sex tape and her deception, he’s furious, inspired to write the tell-all version of Inside, the book he “should’ve written from the beginning.”

At the end of the episode, he invites Georgina to join him at a writers’ retreat in Italy, this time wearing a chambray shirt, jeans, and a cargo jacket. Season one Dan is back, but he no longer wants to enter Serena’s world—he wants to burn it down. 

Season Six

Thus comes the point that the show pivots Dan from Lonely Boy to Gossip Girl. Much like his blogging pseudonym, season six Dan is chameleonic, manipulative. From episode to episode, he dresses most like the person he currently wants to be, to impress.

Let’s take the season one opener: Georgina and Dan are in Italy, Georgina cracking her metaphorical whip as Dan bangs out the Inside sequel on a typewriter. They return to New York to look for Serena, who’s been missing since she slept with Dan.

Georgina tells Dan that finding Serena will be the perfect ending for his book, and so Dan’s outfits mirror his new taskmaster’s: gray tops and black jeans. They locate Serena upstate—she’s been going by, of all names, “Sabrina,” Dan’s Inside character.

In episode two, Dan dresses like Nate: all light blue shirts. Nate wants to serialize Dan’s book on The Spectator’s website, and Dan agrees to sell him the Rufus chapter—once Dan discovers Rufus is sleeping with Charlie (actually con artist Ivy), even his poor father isn’t off-limits.

Dan’s wardrobe shifts as quickly as his loyalties. Following the success of the Rufus chapter for The Spectator, Dan sells the rest of his serial to the more prestigious Vanity Fair. His chapters are bringing him more fame and money and potential sex partners than ever before, and yet he’s not receiving the literary acclaim or love that he’d hoped for. His ties cut with Rufus and Serena and Nate, he asks Blair if he can crash at her place, his bright red T-shirt picking up the vibrant tones in her patterned robe (6.4).

Bubble Episode

And so we arrive at this profile’s deep dive: episode 6.5, “Monstrous Ball.” At the beginning of the episode, Dan has settled into the Waldorf penthouse, having breakfast with Blair and advising her on her designs. She recently took over her mother’s fashion line and is working on a cotillion gown. In this scene, Dan wears a gray blazer and shirt and black pants—the same color palette he and Blair shared at the beginning of their friendship. Blair, more important, is wearing Chuck’s engagement ring around her neck—he’s promised to put it on her finger once he defeats his newly returned father, Bart.

Dan is working on the Blair chapter of his book, but once he sees Blair’s ring, he decides to publish the Chuck chapter first. Blair is infuriated to discover that she isn’t in the chapter, that it focuses on Chuck’s battle with Bart. Dan still wants to win Blair back, and as long as she’s not engaged to Chuck, he thinks he still has a chance.

Dan escorts Blair to cotillion: she in a black sequin gown, a pearl headband, and diamond earrings; he in a black suit, a gray shirt, and, most important, a black clip-on bow tie; his hair slicked back. This time, he’s not imitating Georgina or Nate but Chuck.

After all, Chuck is the character most associated with bow ties; he even wears his own to cotillion: a silver one paired with a white shirt and black tux. Dan, the show is telling us, is the villain; Chuck is the hero; their “badness” and “goodness” represented in the simple dichotomy of dark and light clothing.

At the cotillion, Blair learns that Dan slept with Serena and slaps him. His betrayal, she tells him, is worse than Chuck sleeping with Jenny in season three—a strange parallel for her to draw, as Jenny was drunk and emotionally vulnerable when she slept with Chuck, much like Dan was with Serena. In fact, both Chuck and Serena crossed lines of consent when they slept with Jenny and Dan—Serena, especially, in taping it without Dan’s knowledge. And yet this conversation ends with the most fucked-up, unchallenged line in the history of this show: when Dan (rightly) says that Serena manipulated him, Blair replies, “In order to claim date rape, you have to say no.” Holy shit!

Dan’s suit and bow tie also call back to the look he wore to escort Serena to cotillion. At the end of the night, Serena and Dan commiserate over milkshakes and pie, his clip-on undone, their relationship rekindling as Frank Ocean’s “Thinkin Bout You” plays in the background. What a beautiful song, what a trash fire of a pairing.

The show stuffs the next episode with classic Dan/Serena symbols from seasons one and two. It’s almost as if the show is trying to remind us what we once liked about them, but all they have are superficial, expendable examples: Vespas and pool tables and chocolate-covered strawberries and stuck elevators. The relationship itself is rotten to the center: in order to reanimate Chuck and Blair, the show sacrificed Dan and Serena, turning Serena into a rapist, and Dan into a sociopath—all while holding up its usual twisted ideas about consent.

By the end of the episode, Dan and Serena have reunited, and in episode eight, they’re hosting Thanksgiving together: Dan in a red V-neck sweater and black blazer to match Serena’s red-and-black-print dress. That day, he publishes the Serena chapter, a scathing takedown that calls his girlfriend “a golden shell.” Chuck, Blair, Serena, and Nate kick him out of the dinner, but on his way out, Bart hands him a business card, impressed by his work. It’s just as Dan hoped—he’s becoming Bart Bass, gaining their respect not through love but fear. “They might’ve hated me,” Dan tells his father, “but [in that moment] I was one of them.”

Once Dan learns Serena is leaving New York for good, he tries to make her stay, offering up the good chapter he wrote about her—the one he didn’t publish, hoping the bad one would show he wasn’t “afraid” of her.

By the series finale, Serena has read the chapter and is even more confused: How could Dan write such awful and such wonderful things? In this scene, their outfits complement each other’s: Dan in a black sweater and gray blazer, Serena in a gray tweed coat. He takes her back to the first time they met, the brief conversation he wrote about, five years ago, in his New Yorker short story.

The scene flashes back to a freshman birthday party, Dan dressed in blue plaid button-down and blazer, his hair once again cropped close. He sees Serena at the top of the stairs and they exchange a few sentences, Serena never descending to meet him. She is high on her pedestal, looming above him.

In that moment, he reveals, he was inspired to start Gossip Girl, Serena as his muse. When Serena returned, he penned his first post about Lonely Boy: “If I wasn’t born into this world,” he says, “maybe I could write myself into it.” The whole flashback has an air of retcon, of the writers pulling and plucking from prior seasons to try to make some sense of Gossip Girl’s reveal—freshman Dan and Serena both dressed in outfits that would look more at home in later seasons. Even Serena tries to shoehorn greater meaning into Gossip Girl’s identity, calling Dan’s blog a “love letter” to all his friends.

Five years later, Dan and Serena marry at Chuck and Blair’s home, Dan in a gray tweed suit with black lapels, black tie, white shirt, and calla lily boutonniere. Serena looks like she’s dressed for a different wedding: jeweled drop earrings and a strapless ball gown, the bodice gold. Unlike at their first meeting, she descends the stairs, taking Dan’s hand at the bottom. He has finally gotten what he long wanted: to earn a permanent place on the Upper East Side, to meet Serena as an equal. And yet, what has Dan really gained? How has he changed, and how has Serena? She’s still encased in a golden shell, filling herself with scraps of chapters and blog posts and short stories, convinced they are love letters.

The camera pans from the wedding to the street below, where the next generation of Upper East Siders flocks together. We follow a Dan-like boy outfitted in a cargo jacket, satchel, and khakis; a Serena-like girl smiles at him, and a Chuck-like boy scowls. “There will always be someone on the outside wanting to get in,” Gossip Girl tells us, and we are left with the idea that the show has planned this all along, that Dan was Gossip Girl from the first moment he slung on that cargo jacket. But the truth is, in time a hero can become a villain, a love story can become a horror story, and all it takes is a little revision. 

[We’ve come to the big three: Serena, Chuck, and Blair. Since these characters have the most complex fashion on the show, I’ll deliver the remaining profiles every three weeks. Serena’s will arrive on Thursday, 4/1.]

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: What else has Penn Badgley been in?

CL: You.

DP: No, he’s never been in me.

————

DP: I don’t trust people who go by Dan.