Season Four
[This profile contains discussion of sexual assault.]
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 with 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.