The Revision of Dan Humphrey
[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 becomes 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 is 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.
[Part two, covering season four through the series finale, will arrive in your inbox this evening.]