Gossip Girl may have been advertised as the most scandalous show on television, but it turned an entire generation of tweens into tiny sartorialists, so it's really an educational programme. Because we're gluttons for punishment, we decided to choose eighteen iconic outfits from the series to represent Gossip Girl's best fashion moments. It's a hard job, but someone's gotta do it. You'll notice there are *tons* of spoilers below, and we've entirely omitted Vanessa Abrams and Dan Humphrey from this list because they're trash characters with horrible taste. Sorry, not sorry.
Gossip Girl season two introduced us plebs to the concept of a Hamptons white party, which unfortunately describes both the clothing and all of the attendees. Serena van der Woodsen wore the summer's hottest accessories, an elaborate head chain and Nate Archibald, and we've been trying to recreate the enduringly beloved look ever since. While her Grecian-inspired Oscar de la Renta dress is ostensibly the star of the show, it's the golden girl's up-do that keeps us coming back to this 'fit nearly a decade later.
Blair Waldorf wore a stunning Marchesa gown to her prom, proving definitively that she had more style in her pinky finger than the rest of us have in our entire bodies and that this show hasn't aged super well. For anyone who's been living under a rock, a quick recap: Marchesa was founded by Georgina Chapman, the wife of living garbage pile Harvey Weinstein. On the one hand, Georgina accidentally married a scumbag and decided to make a Marchesa for JC Penny fashion line. On the other, she outfitted Constance Wu in Crazy Rich Asians's out-of-this-world wedding scene. Do with that information what you will, but this gown is objectively gorgeous.
How could anyone look so dour in this burgundy bandage dress? We don't remember why Serena looks like she's been stood up by Shawn Mendes (the *only* reason someone that beautiful could have to be this pressed), but this look exemplifies how Serena elevated the bandage dress to an art form. Hervé Léger should be paying Blake Lively commission for every dress he sells because the promise of having legs for days like Serena is his brand's primary appeal to the under-30 crowd.
We can't really blame Gossip Girl for Jenny Humphrey's style devolution — Taylor Momsen dug that grave herself, then wrote seven grungey songs about being buried alive. Sometimes the bold choice isn't the best choice, Little J. On season three, the producers were still trying to give Taylor a tenuous grip on reality by mixing her personal "style" with Gossip Girl's aesthetic, and it wasn't horrible. This stunning Blumarine cotillion gown would never fly at an actual coming out, but it marks the most perfect blend of couture and punk GG ever came up with. Vivienne Westwood would be proud. Still, it was all downhill from here for our least favorite social climber.
Leave it to Blair Waldorf to show up at a black and white ball in a red slip dress. Most of this episode was wasted on an elaborate scheme by Jenny and Juliet that involved pretending to be Serena by wearing the same dress as her and happening to be blonde, which worked because none of these characters are ever sober for long enough to use any deductive reasoning skills. Blair matches her bad boy BF, who also chose to wear red to the party completely independently of Blair's plan. A match made in hell heaven? Blair can dress like Kate Middleton as much as she likes — we all know she's a Pippa at heart.
This ethereal golden dress and rare curly hair moment make Serena look like she belongs on a Greco-Roman fresco as an actual deity to be worshipped. She's also lowkey rocking the same outfit Khloe Kardashian wore to Diana Ross's 75th birthday party, but without the weird racial undertones. You go, Serena! Statement necklaces were having a big moment in the '00s, and this is one of the rare occasions when we still support it. Serena's upscale sartorial bohemia is on full display here, and we wouldn't have it any other way.
We aren't saying that statement tights need to make a comeback, but we miss the old Jenny Humphrey. Before Taylor's weird teen angst completely took over her character, Little J knew what was up. Gossip Girl saw many, many inventive takes on the Constance Billard dress code, but Jenny's preppy color blocking interpretations were some of the best. We're still obsessed with her blue ruffled ankle socks and the skillful red, white, and blue color story that looks more prestigious than patriotic. Don't even get us started on that white coat — remind us how she was supposed to be poor, again?
It's too bad that art imitated life for Ed Westwick. Ed has come under fire due to sexual assault claims, but unlike Chuck Bass, he hasn't gone through seven seasons of televised redemption and character development. It kind of makes you think about the stuff we all let television characters get away with and what that says about our true values as a culture. Anyway, this teen Hugh Hefner blazer is amazing, and Chuck was honestly the best-dressed character on this show. Exhibit A: His striped socks. It's all about the details.
Chuck Bass went to Germany for Blair's Falke stockings and Paris to buy her favorite macarons because it isn't love without gifts and peonies. This scene still makes us cry, but we're not sure if it's because of Chuck fulfilling all of our "f*ck boys can change" fantasies or Blair's stunning coat. No one else could pull off green and gold with panache, but this outfit couldn't have been done any other way. Blair inspired us to bring springtime to New York even when it's still overcast and raining because true style icons control the weather instead of letting the weather control them.
The show may have tried to keep them apart, but Serena and Blair are better together. Ghost designer Abigail Lorick was the brains behind these "Eleanor Waldorf" designs, and the backless frocks make us wish these drastically different BFFs blended their styles more often. This impromptu Plaza photoshoot remains one of the best scenes in Gossip Girl's first season, and not just because it deserves an award for most interesting use of a belt. We would never think to use a slim belt to cinch and adjust the silhouette of a backless gown, but that's why the GG costumers are fundamentally better than us.
At first, we thought the pattern on this twisting gown was just a simple reimagining of an Hermés scarf, but it looks like Taylor Swift might have stolen Georgina Sparks's aesthetic because this b*tch seriously made her reappearance in the New York fashion scene wearing a gown of snakes. Talk about truth in advertising. The most frightening queen of the Upper East Side knows exactly what she's doing, and even if you don't agree with her methods, you have to admire her strong sense of self-awareness.
Gossip Girl really tried to make lace tights happen, and it shockingly worked. While the clingy lace overlay only really *looks* like tights, we're pretty sure it still counts. The belt-turned-train is what really ties together one of Serena's best-remembered formal looks, but the devil is in the details with intricate beading over the dress's lace that comes across as classic elegance instead of tacky or over-the-top gaudiness. Literally, how. This was actually a Ready-To-Wear look from Zuhair's Fall 2010 collection, lace and all showing how GG and the fashion world grew in a beautiful symbiosis during its final seasons.
Google "Chuck Bass Signature Scarf" and you'll literally find dozens of photos of this exact patchwork polka-dot silk scarf. If only Chuck was an actual person who could have shown up to the 2019 MET Gala and shown these boring men in black suits how to actually pull off a metrosexual camp look. Chuck was one of the formative sex symbols of the '00s (RIP us, honestly), and he was never afraid of rocking some purple or a statement accessory. Fans have actually recreated this scarf on fan-made sites like Redbubble because real respects real.
We were originally taken by the textured pattern on Blair's golden bodice and an ombré vibe that was honestly ahead of its time, but then we found this photo of our gorgeous leads on a casual catwalk. Again, the color stories on this series, not only with individual outfits but also within entire scenes, are inspirational. These blues both carry undertones that are complimented by Blair's golden bodice without actual being remotely similar to each other, providing a cohesive aesthetic without being too matchy-matchy.
Gossip Girl seemed to exist in a wonderful eternal fall because it never ~really~ snowed or rained, and the show made a huge effing deal of it whenever they wanted to show a summertime story. Naturally, this means the characters wore a revolving door of fabulous coats of questionable practicality. This was one of the best casual coat 'fits from the show, with Serena sporting an early take on lampshading. Ariana Grande is quaking. Her leather thigh-high boots and plaid tights scream "I'm youthful and *definitely* a teen, I swear!" while her purse just spit at me and called me middle class.
While our last Georgina Sparks moment showed the schemer embracing her true self, we almost thought this still was of Dawn from Buffy The Vampire Slayer because it's the exact opposite of Georgina's leather and lies aesthetic. The look on her face makes us think this wasn't from her brief born-again Christian phase but a good manipulator can become anyone she wants. Here, Georgina wanted to be an innocent prepster who can effortlessly match her lipstick to her accessories. Is it possible that Georgina can wear a Blair Waldorf headband better than the queen of Constance herself?
Everything Elie Saab touches turns to magical, ethereal femininity. Somehow, we expected nothing less from Blair Waldorf's shotgun wedding dress for her impromptu Central Park ceremony. This gown has all of the hallmarks of an Elie Saab original: delicate details, a translucent base, and the very real possibility that it was woven together with fairy dust and love. Blair's turquoise and silver earrings accentuate the dress's pale coloring, while her wedding-appropriate headband is both on-theme and a final theatrical element to a performatively elegant wedding look.
Classic S just *had* to one-up B, didn't she? Literally, the only dress on GG that could edge Blair's wedding dress out of the top spot is this George Chakra gown for Serena's own wedding. She gets a few points removed for marrying her high school bully and step-brother, but the hunter-warrior goddess Diana couldn't even pull off this feathered golden masterpiece better than Serena van der Woodsen can. An honorable mention goes to Little J in the back wearing a golden dress that's actually gorgeous and compliments Serena's nicely without drawing focus (see what we said about color stories!), and as an added bonus, she isn't wearing an entire tube of eyeliner for possibly the first time since she hit puberty. Way to ride those coattails, J!