Say hello again to your favorite Upper East Siders and goodbye to headbands. HBO Max’s Gossip Girl reboot is here. And while some things are very much as you remember them: Kristen Bell’s haunting narration, classism, adults in their late twenties playing teenagers, a new order is under foot at Constance Billard. For one, social surveillance is served in the form of an Instagram account, not a blog. Nine years in the future, the characters are notably not all white and straight.
Whether Gossip Girl was the reason you moved to New York or just the reason you felt the need to wear a massive belt over a floral dress, the show single-handedly shaped the sartorial zeitgeist of the 2010s. Thanks to the show’s iconic costume designer, Eric Daman, fashion will remain the true main character in the hit series. The series premiered alongside a twenty-two look runway show by industry powerhouse Monse. Keep scrolling for eight outfits inspired by the leading looks from Gossip Girl’s reboot.
Zoya Lott (Played by: Whitney Peak)
New to town and staunchly the group’s outsider, Zoya enters the first episode as a freshman at Constance Billard. Her sincere take on the school uniform is quickly deconstructed by what is casually referred to as “The Samurai Seven.” The crux of the drama, the Serena vs. Blair, if you will, in the new version is between Zoya and her half-sister, Julien. Upon meeting in person for the first time, Julien authoritatively pulls the scarf acting as a headband off Zoya’s head and ties it around her neck. Note taken!
Zoya’s style starts as timidly as she does, until two nights out where she opts for shimmering bodycon numbers. A fashion transformation awaits, undoubtedly. Until then, high socks and plaid skirts it is.
Julian Calloway (Played by: Jordan Alexander)
Half-sister to Zoya, influencer to millions, Julien is presented in the pilot episode as the latest incarnation of Serena van der Woodsen. Her fawning friends prep her lighting and adjust her bag’s positioning to keep her camera ready. There’s lots to look forward to in the show at large, but Julien’s looks seem particularly promising. By the end of the first episode, she’s walking in a full Christopher John Rogers runway show.
Incorporating Julien’s signature white boots give any look a boost. The plethora of designer bags she carries don’t hurt, either.
Max Wolfe (Played by: Thomas Doherty)
Enter Max Wolfe, a sauve, pansexual pot-stirrer with strong hints of Chuck Bass. His charms precede him, as does the wolfish smile his predecessor made famous. Showcasing impressive versatility early on, the character of Max holds a keen amount of potential for consistent style over the course of the show. He’s preppy with a twist of something more modern and playful than the Uptown landscape he finds himself in.
Embrace a statement top, keep the bottom half simple, and finish off the whole look with a fanny pack/crossbody style bag.
Audrey Hope (Played by: Emily Alyn Lind)
Queen B could never be replicated, but the reboot’s Audrey Hope comes pretty close. The perils of her monotonous monogamy are explored in the first episode, but pale in interest compared to the looks she’s already serving. Like her inspiration, she loves a hair accessory. But unlike Blair, she favors an oversized silhouette in many scenes, highlighting her impossibly long legs.
Take a page from Audrey’s book by pairing a large sweater over a more buttoned up look, legs out, for the ultimate “bending the dress code” moment.
Obie Bergmann (Played by: Eli Brown)
Somewhere between Nate Archibald and Dan Humphrey sits the new character of Obie. While he’s introduced as Julien’s boyfriend, viewers can’t help but wonder for how long. Beyond his complicated romantic life, Obie spends time protesting and volunteering. His outfits seem to come with an agenda to appear down to earth. And it works, if your idea of earth is just monochromatic earth tones.
Embrace natural, warm hues and create outfits of a single color. Accessorizing with a canvas messenger bag is certainly optional.
Aki Menzies (Played by: Evan Mock)
Quiet and discerning, Aki sticks out like a sore thumb in his blatantly confident crew. While his pink hair and streetwear style feel very of-the-moment, there’s something a bit coy about his whole presentation. And like every Eric van der Woodsen before him, when he says, “I don’t like to stick out,” it feels like a code to watch his every move.
Try baggy jeans with a freshly ironed hoodie and sneakers for a look more at home in Brooklyn than the Upper Eastside.
Monet de Haan (Played by: Savannah Smith)
Behold the wildcard, aka this cast’s Georgina Sparks, Monet. Wealthy and never without a designer bag, this character’s look hinges heavily on polish and poise. She’s fearless, showing a huge range beyond her comfort zone, which seems to be matching sets. In one scene, she’s shown in a satin purple blazer with shoulder pads.
Lean all the way into posh dressing with a matching tweed set. Just hope your best friend is more charmed than the teachers seem to be.
Kate Keller (Played by: Tavi Gevinson)
Fashion’s darling Tavi Gevinson plays a fed-up teacher at Constance Billard. In the first episode she complains about the hour it took her to plan her outfit, only for her students to prove her wrong in one second. Tough luck, Miss Keller. These students are ruthless, but the new Gossip Girl seems to imply that the teachers just might be, too.
Channel the twenty-something in a crowd of well-dressed teens by sticking to high necklines and trusted basics.