[This profile contains discussion of suicide and sexual assault.]
Season Three
Serena spends the summer partying across the globe, all while hiding her exploits from her family. She and Carter did find her father, but when he didn’t want to see her, she decided to become inescapable, a tabloid fixture. Her wardrobe, too, suddenly seeks the attention she craves. Season three Serena, says Daman, is a return to “the old party-girl Serena, that girl who kind of overdoes it a little and is trying to get attention through her clothing” (“Gossip Girl Style with Eric Daman”).
She returns to New York, still pursued by the paparazzi and Carter. While she’s happy to be photographed, she’s avoiding Carter, who wants her to stop justifying her father’s rejection. To escape Carter, she undoes the ties of her pale blue halter dress, attracting the paparazzi with her wardrobe malfunction.
Carter follows Serena to a polo match, where her infamy has somehow earned her the first ball throw. There, she wears a Grecian gown, much like the one she wore to the White Party a season ago. The color, however, is an eye-catching orange, perfect for stealing a horse and riding it in front of photographers.
By episode two, Serena is having doubts about Brown. She doesn’t know what she wants to do with her life—and, I think, doesn’t know how to live outside New York, a city where everyone knows her name. Instead of leaving for Providence, she crashes at Chuck’s apartment and quickly ruins one of his business deals. “Train wreck,” he mutters, and almost as proof, she takes Carter to interrupt another of Chuck’s business meetings, this time at a bar. Again, she goes for solid, bold color—a cowl-neck royal-blue dress and layered gold necklaces. This is old Serena at her peak, reminiscent of the bright green dress she wore in the Thanksgiving flashback.
In episode four, Lily returns from taking care of CeCe, and Serena must finally tell her that she’s deferred Brown for a year. Suddenly, Serena is dressed like she’s in early season two: a brown tank and jeans, a very Lily-like turquoise necklace. It’s as if she’s trying to prove, through her wardrobe, that she’s not old Serena, that’s she’s still the Serena who received a personal invitation to Yale.
To show her seriousness to her mother, Serena interviews with Tory Burch, Marchesa, and John Porto Gallery. All reject her; as Serena says, they’d rather she attend their parties than work for their companies. For all her interviews, she wears a gray blazer thrown over a gray tank, lavender bandage skirt, lots of red beaded necklaces, and lipstick—a rare formality for Serena. She looks as if she’s approximating office wear, as if she’s pieced together a look from her usual clubbing and casual wear. After all, none of the close women in her life work—not Blair or CeCe or Lily.
At lunch, however, Serena meets a publicist, K.C., and impresses her with her deft handling of her client. Suddenly, Serena has a job that makes use of her fame, her connections. She even works a premiere in a silver-sequin bandage dress, a gray blazer on top. Her professional style, from here out, is “throw a blazer on it!”
Serena parlays her PR experience into a job working for Nate’s cousin Tripp van der Bilt (3.9), recently elected to Congress and married to Maureen. For the interview, Serena wears a variation of her first interview look: a black blazer, tank top, chunky statement necklace, and miniskirt. Just as her first job was a way to prove herself to Lily, this job is a way to get closer to Tripp. What kind of PR professional is Serena, anyway, when she’s about to participate in a public relations nightmare?
Serena and Tripp flirt for a few episodes, kissing after Tripp discovers one of Maureen’s machinations. All three attend Thanksgiving dinner at the van der Woodsen penthouse (3.11), the outfits from which I discussed more thoroughly in Lily’s profile. Lily is disappointed in her daughter for seeing a married man but not as disappointed as Serena is when she finds a letter from her father. Lily was with William that summer, when Serena was trying to see him.
Serena and Tripp run away to the van der Bilts’ country house; Tripp is planning to divorce Maureen. She gets to him first, asking if she can present an idea to Serena (3.12): she’ll stay Tripp’s wife, and Serena will become his mistress. “It’s a time-honored political tradition,” Maureen explains. “I’m Jackie [Kennedy]. You’re Marilyn [Monroe].” When Serena objects, Maureen shows her the letter from William, wondering how Rufus will react to discovering Lily is a “cheating whore.”
The scene’s outfits only reinforce Maureen’s proposed roles. She is Blair-like, practiced, precise, in a structured hat, tailored green coat, and plaid scarf; Serena is soft, sensual, in a low-cut gray sweater, tan jeans, gray shawl, gold necklaces, and diamond studs—the same ones, I think, that she wore in the Thanksgiving episode, that remind the viewer of Lily. Maureen sees them as one and the same, as temptations and home-wreckers.
After Tripp almost kills her in a car crash, Serena turns to Nate, who’s long been waiting to date her. They begin seeing each other in episode thirteen, but Blair advises Serena to take things slow. Their conversation is riddled with talk of “control,” of Serena as a sundae that Nate will gorge himself on after years of hunger.
In episode fifteen, Jenny decides to lose her virginity to her drug-dealing boyfriend, Damien; both Nate and Serena try to discourage her. Unaware he’s on speakerphone, Nate tells Blair that losing her virginity is a “huge deal for a girl like Jenny”—implying to the listening Serena that it wasn’t for her. In this scene, she is getting ready for an event in a black slip and gold robe, the color calling back to the dress she wore when she and Nate first slept together.
Serena changes into a black lace dress, not unlike the one Jenny is wearing—a sympathy between them, a common public obsession with their purity. Stories of Serena’s sexual past keep following her, tainting her present relationships:
Nate: Everyone knows the stories about Adam Handler, Jake Henderson, Matt Price, the art teacher from Prague.
Serena: I didn’t sleep with all those guys, Nate. Haven’t you heard of locker-room gossip? They lied or exaggerated.
Nate: Serena, I lost my virginity to you on a bar at the Campbell Apartment.
Serena: And somehow that reflects poorly on me and not you? Talk about a double standard.
Though Serena and Nate make up by the end of the night, distrust follows them for the remainder of the season. In episode eighteen, Nate discovers that Serena has been secretly meeting Carter. She hasn’t yet told Nate that she’s still looking for her father, and he assumes the worst. Serena even leaves a wedding to follow Carter to Palm Beach, abandoning him once she learns that he’s been stringing her along, hoping they’ll get back together. Her look for the wedding—a blue long-sleeved dress with a white-and-green beaded necklace—is much looser and more conservative than usual, as if she’s trying to convince Nate that she’s not what he thinks she is.
The outfit becomes even more significant when Serena arrives at her father’s Palm Beach hotel room. The door opens to reveal Lily, mirroring her daughter in a V-neckline and green beaded necklace. It was Lily, not CeCe, who was sick last summer, and she’s come to William for her six-month checkup.
By episode twenty, Serena is back in New York, happy again with Nate and bonding with her father. For brunch at the penthouse, she’s bright in a turquoise sheath and pink earrings, coordinated with Lily’s own bright pink sheath. When William asks her about boarding school, she lies about her wild days there, worried that her father won’t love her for all she is. At the end of the episode, she finally tells the truth, and he allays her fears.
Because who is William to judge? He has his own secrets, chiefly lying to Lily about her relapse so he can remain close to her. He even conspires with a co-op member to say Rufus cheated on Lily—all the proof Serena needs that her parents should get back together (3.21).
Serena attends a gala at the New York Public Library, her parents in tow. She’s angry at her friends, and especially Nate, for being suspicious of William. For the first time since season one, she wears a full gold dress, ascending not just to another’s fantasy and desire but to her own: the dream of a perfect, whole family, a loving, admiring father.
When William realizes his secret is about to be revealed, he skips town. Serena goes after him, not believing that he would leave her again. She lets him go before the police arrive—called, against her will, by Nate.
That night, Serena turns to Dan for comfort, drinking and kissing at the Humphrey loft. When Nate finds out, they break up, Serena left to decide if she wants to mend things with him or start over with Dan.
As she and Dan wait at the hospital, Blair’s maid Dorota in labor, they look at the babies in the nursery, baffled by the fresh starts before them. Dan points to one: “She’s going to grow up to have fabulous hair and a great smile, but her daddy issues are gonna make it real hard for her to trust people.” And I mean, who could resist that? The fantasy of Serena is slowly starting to flake, to reveal the real pain beneath her golden exterior—all reduced to two body parts and a man’s absence.
Season Four
Blair convinces Serena to spend the summer in Paris—Blair ruling the Right Bank, Serena the Left Bank. Serena occupies herself with Parisian men—becoming, as Gossip Girl wryly notes, “a muse to us all.” This line is layered over a shot of Serena in an oversize striped button-down, sketching a naked man; any artistic interests still defined by her interest in men.
Though the shirt is likely borrowed—much like Nate’s button-downs in season three—her other fashions are singular. Daman went all out for the Paris episodes, dressing the girls in bright and glittery designer confections. Take, for example, this sharp-shouldered gold blazer, paired with a white striped tank and bright blue pants.
And yet, Serena’s story lines in Paris are very much rooted in New York: Should she choose Dan or Nate? Should she go to Columbia—her father’s alma mater—even though Blair is transferring there? While Blair eventually agrees to the latter question, the former is answered for Serena—when she gets back to the city, Dan is dating his longtime friend Vanessa, and Nate is dating a new girl, Juliet Sharp.
Juliet is a fellow Columbia student and the key master at Hamilton House, an exclusive on-campus society to which Blair wants admittance. On their first day at Columbia (4.3), Serena and Blair go to Hamilton House, hoping to both receive a key necklace—Serena in a brown-and-pink patterned dress and woven belt, in step with Blair’s own brown dress. Juliet, however, says she has only one key left—and it’s Blair’s.
The key itself is a silver Tiffany pendant, more in line with Blair’s taste than Serena’s, but the rejection still hurts. Serena suspects Juliet is withholding her key, and when she confronts her, Juliet says that Blair told the Hamilton House alumni committee about Serena’s “sex tape”—much as she did when they visited Yale. Yet again, the night of the Shepherd wedding follows Serena. Blair and Serena soon learn that Juliet is lying, and Serena receives her rightful key. The friends believe Juliet is jealous of Serena’s past with Nate—but as we’ll discover, Juliet’s revenge goes so much deeper than that.
Serena is repeatedly late to class thanks to a man who steals her cabs to send off his one-night stands—and flirts with Serena in the process. When Cab Man first appears (4.5), Serena wears a bright yellow vest-like top, yellow flower hairpin, blue shorts, and gold chain necklace—the return of Serena in yellow signaling desire.
Later that day, Gossip Girl sends out a blast saying Serena has an STD, and Serena suspects Juliet submitted it. Serena begs Nate not to get tested right away and confirm the rumor, but then another blast drops with a photo of both Dan and Nate at Columbia’s health clinic.
When Vanessa sees the photo, she confronts Serena, accusing her of sleeping with Dan that past spring. “Let’s just say it wouldn’t be the first time a guy has lied to his girlfriend to cover up a night spent with you,” Vanessa says—alluding, of course, to the first time Nate and Serena slept together.
That evening, Serena attends a party at Hamilton House in a cream cocktail dress with gold trim. More importantly, she’s wearing diamond studs and a bun—the pairing she goes to when she wants to be her most proper, most Lily-like self. She wants to prove to her classmates, to her professors, that the rumor isn’t true, that she is unsullied. For that is the implication of Vanessa’s reaction—that Serena’s supposed STD is a mark of her immorality, her sleeping with Dan and Nate when they were dating other girls.
At the party, Juliet steals Serena’s phone and sends an email to her professor, offering sex for grades. When the dean and professor confront Serena with the email, Juliet sets up Vanessa to take the blame.
Serena heads back to the Upper East Side, where she runs into Cab Man at a bar; they spend the night talking. “I thought I could start over,” she tells him, “[but] my past seems to follow me.” Indeed, Cab Man—or Colin—is also a reminder of her past, of a relationship with a teacher that almost went too far. As she discovers the next morning, Colin is the professor for her new business class.
Serena plans to drop the class and date Colin until Lily shames her into taking it (4.6), needling her daughter’s intellectual insecurity by implying the subject might’ve been too difficult for her. Serena and Colin agree to pause dating until the class is over; they get to know each other through regular office hours, Serena throwing a tan blazer over her body-con blue dress (4.7). As it was in season three, her blazer is a stab at professionalism, her seriousness as a student, even as she and Colin struggle to wait six weeks.
At Blair’s birthday party, they almost break their agreement, Serena yet again in a yellow gown and giant gold necklace, bright against the other main characters’ dark reds and purples and blacks. By the next episode, Colin quits his class for Serena, kissing her in front of all of society at the New York City Ballet. Juliet tries to use their relationship to get Serena expelled, but Serena’s friends rally around her instead. She and Colin ultimately break up, and Serena is presented with the same question from the summer—Dan or Nate, both recently single.
Serena struggles to choose between the two men and even between two dresses for Chuck’s Saints and Sinners party (4.9). Ultimately, she goes with Saint in a lace mask and gray-blue Carolina Herrera gown, the color tying her to the one she really wants—Dan in his light gray suit. Unfortunately for Serena, Juliet and Jenny are also wearing the dress; they’ve teamed up with Vanessa to impersonate Serena at the party: Juliet kissing both Dan and Nate; Jenny humiliating Blair. Unbeknownst to Jenny and Vanessa, Juliet is planning an even crueler revenge; at the end of the night, she drugs and dumps Serena at a motel.
When Serena is found a few days later, Lily checks her into the Ostroff Center (4.10); everyone except Dan believes that old Serena has returned. “She’s not just the beautiful teenage girl you saw at some party anymore,” Lily tells Dan. “She’s a troubled young woman avoiding some very real consequences.”
Serena, too, has difficulty believing her behavior, though she notes it’s not without precedent. In therapy (4.11), she says, “This wouldn’t be the first time I’d been with two guys in one night or betrayed my best friend.” The scene flashes back, as expected, to the Shepherd wedding, to Serena running away to boarding school. For the first time, we receive glimpses of her life, her wardrobe, at Knightley.
Like Constance, Knightley has a uniform, which appears to include a blue button-down and red-and-gold tie. Serena wears her tie loose, her shirt collar undone, layered with a sparkly blue cardigan, gray tweed shorts, and diamond-patterned tights. She’s still the wild Serena we saw in the Thanksgiving episode, drinking absinthe and paying her classmates to do her homework. That is, until she meets Mr. Ben Donovan—save for Miss Carr in season two, the only teacher to take her seriously as a student.
Around Mr. Donovan, Serena’s ties are still loose, but she wears them with collegiate blazers and plaid button-downs, mirroring his. It’s almost like she’s trying to look the picture of the perfect prep school student to impress him, to show him she wants to do well.
One day, Ben drives Serena to Vassar Library; his car breaks down in the rain. They stop at a bed-and-breakfast for help, and Serena asks him if they can get a room. He turns her down—becoming, perhaps, “the only guy to say no to [her],” as she later tells her therapist.
In this scene, she wears the standard Knightley blue button-down with a black-and-gray argyle cardigan. Reader, I gasped—an argyle cardigan being the same piece that Dan and Serena traded back and forth in season one, that Miss Carr wore after she had sex with Dan in season two. This piece is drawing parallels between the stories, between these two inappropriate teacher-student relationships.
Still, not everyone believes that Mr. Donovan said no. When Serena returns to the city, Lily tries to get her daughter back into a private school, but no one will take her after seeing her dismal records at Knightley. Lily uses a rumor about Serena and Mr. Donovan as leverage against Knightley, not realizing that the school will take criminal action. She forges her daughter’s signature on an affidavit, and Ben Donovan goes to prison believing Serena has lied. Hence, he and his sister, Juliet, take revenge on Serena, aiming to leave her with as little as Ben has.
Once Serena learns what her mother did, she visits Ben in prison, wanting to do whatever she can to help him. Lily, too, works to get Ben out on parole—having believed, all this time, that the rumor about her daughter was true. The Humphreys offer Ben a room at the loft, and Serena strikes up a friendship with him, even begins dating him in episode fifteen.
Throughout these episodes with Ben, Serena wears a lot of grays and other neutrals paired with more glittery elements—the former meant to soften and dull the latter. In episode fourteen, for example, she wears a gray vest over a gray sweater and sparkly skirt, rhinestone necklaces on top. As much as she tries to relate to Ben, to his more humble background as a Knightley townie, she is still the daughter of the woman who put him behind bars, and she can’t help but remind him of the wealth and privilege that brought them to this point.
Ben and Serena ultimately break up, and Lily turns herself in for her forgery, her sister, Carol Rhodes, sweeping into town with her own daughter, Charlotte (4.18). Carol raised Charlie in Florida to shield her from the Upper East Side, and Serena is determined to show her cousin another side to her world. She even gives Charlie the necklace off her neck—a “family heirloom,” she says. Naturally, it’s gold.
Charlie stays in the city and quickly learns to navigate Gossip Girl; she helps Serena follow Dan and Blair, whom she suspects are seeing each other (4.19). They’re really only friends, Blair secretly dating a prince of Monaco, but Serena is still angry at Blair, sure that any appeal Dan has for Blair is only because he is “hers.”
“You would see it that way,” replies Blair, “because it’s always about you, isn’t it? I’m sorry to break it to you, but Dan and I have a real connection. We did things like visit the Dia and debate Chabrol versus Rohmer. Things we could never do with you.” Just as Lily did earlier this season, Blair strikes one of Serena’s deepest insecurities; she may inspire art, but she lacks the knowledge, the confidence, to speak to it.
Charlie begins seeing Dan, which, strangely enough, seems to bother Serena less than the idea of Blair dating Dan. That is, until Charlie steals Serena’s most iconic dress, her gold cotillion gown, to attend a Constance fundraiser with Dan. Serena herself is in a coral gown with silver accents and earrings, only second-best.
At the fundraiser, Serena runs into Headmistress Queller, who is disappointed to learn that her old student is attending Columbia, not Brown. “I know I was always hard on you, Serena,” says the headmistress, “but it was only because I thought you could become something. I’d hoped you’d leave New York, see the world. Maybe find your place somewhere far away from all this.”
Soon after, Serena is accosted by the minis, now all dressed as little Blairs. “How could you not end up with Nate or Dan?” asks the one who once dressed like Serena. “I used to want to be like you, but now I want to be like Blair.” In the halls of her old high school, Serena is haunted by her past mistakes, culminating in a confrontation with her doppelgänger, Charlie.
Charlie, Serena learns, has stopped taking her psychiatric medication; she finds her cousin in a classroom upstairs, a window open. It’s like Serena is staring at her high school self, Charlie’s hair done in a simple ponytail, just as Serena did hers. Only Charlie’s earrings are different; she chose a larger statement earring, more at home in the current Serena’s jewelry box.
“[Being me] doesn’t mean what you think it means,” Serena tells her cousin. “All night, I’ve realized I didn’t choose college. I never chose between Dan and Nate. I didn’t even choose Paris last year.” She’s repenting to the girl she once was, who made active choices. Charlie climbs down from the window and comforts her, and they return to the penthouse together. Little does Serena know, Charlie is actually Ivy Dickens, an actress hired by Carol to gain access to her daughter’s trust fund. Charlie’s mental health struggles were all performed, meant to prevent the family from seeking her out in Florida.
Serena decides to stay with CeCe in California for the summer: “I needed to make a choice,” she tells Blair, “and I choose me.” On a beach, a sarong and denim jacket over her suit, she comes across a man reading her favorite book, F. Scott Fitzgerald’s The Beautiful and Damned. (“I relate to it,” she says, “more than I should admit.”)
The man, Marshall, is scrambling to put together a scene-by-scene comparison of the book and movie script for a meeting, and she offers to help. Then the director, David O. Russell, appears and gives her a job—calling Serena “the beautiful” and Marshall “the damned.” Serena’s finally found work from, yes, her beauty and timing, but also her own knowledge and experience—a sign, perhaps, of promising things to come.
[Thank you for hanging on through this longer profile! The last part, covering season five through the series finale, will drop tomorrow morning.]