The Most Iconic Outfits From 'Gossip Girl'
'00s fashion at its most dramatic.
It's hard to overstate the influence of Gossip Girl (we are, of course, talking about Blake Lively and Leighton Meester-fronted original, not the eventual remake). The show remains a '00s and early '10s sartorial time capsule, like Sex and the City for teens, with couture incorporated into plotlines and personalities in ways we hadn't seen since SATC.
From Serena (upper-class boho) to Blair (preppy chic) to Jenny (tween chic, then punk princess), every character in Gossip Girl was clearly identifiable through their wardrobe choices. Costume designer Eric Daman called the show a "fashion monster": its influence—and access to designers—only grew over the course of its six seasons. Ahead, the most iconic outfits.
"Casual" Stroll
One of the funnier aspects of the show was its interpretation of "casual walking around Brooklyn" outfits. Chuck Bass (Ed Westwick) and Lily van der Woodsen (Kelly Rutherford) looked like they were coming from a brunch at the Ritz in this photo. The different, but complementing, patterns on both their outfits was a nice character synergy.
High-Low
This photo, from 2009, showed off one of Gossip Girl's most iconic shooting locations (the Metropolitan Museum of Art steps). It was also, for Jenny Humphrey (Taylor Momsen), right in the middle of her evolution to a more overtly "punk" style: the simple oversized tee contrasting with the "tougher" fishnets and studded bag.
We're Going Shopping
Gossip Girl had clothing in its DNA, and that was sometimes literalized in shopping montages. I found it hilarious that anyone would choose to shop in a minidress with such complex fringe on the shoulder. But if anyone was going to accept a sartorial challenge, it was Blair Waldorf (Leighton Meester).
Luxe Leather
Serena's fashion was so, so interesting. In her non-school life, she was very elevated boho: big bags, long hair, floppy hats, and soft dresses over structured blazers. But in her "uniform" clothing, her aesthetic had to show up in different ways, like this shrunken leather jacket.
Summer in the City
As with Sex and the City, some of the show's most interesting outfits were complementary. This was most obvious in the case of Serena and Blair, who had fairly opposite vibes that came together nicely: Blair in a floral A-line dress and Serena in a funkier, simpler shift.
Out of Office
Listen, you still had to wear couture even when you were at the beach! Serena looked ready to lounge and head to the after-party at the end of the night simultaneously. That dolman-esque sleeve was very of its time, as were the studded sandals, but the bag was chic as heck.
Non-Basic Black
This shot from 2009 exemplified the best of Jenny's particular aesthetic. The simple black outfit was relatively neutral, but the accessories made it shine. That short-sleeved coat, cool braided bag, miniskirt, and contrasting navy booties pushed the look fully into "high fashion rebel."
Like Mother Like Daughter
Watching the show play with the mother-daughter dynamic between Lily and Serena was actually quite fun. The near-match of their dark denim (Serena in skinnies and Lily in cigarette pants) and complementary beige tops made it very clear where Serena got her influences from.
Red Hat
Gossip Girl in winter meant very chic coats. That worked especially well for Blair's style, which leaned towards the structured and polished anyways. This combination of gray plaid in the coat contrasting with the red fedora hat and red Chanel bag was inspired.
Gray Lady
This photo, taken in 2010, showed Jenny towards the later end of her transformation into more adult style. This was also proof that, while the Gossip Girl costume designers excelled at color and pattern mixing, they could achieve a striking look using variations on a single hue.
Cocktailed
The "night out" look for the Gossip Girl characters was a thing of beauty. Unlike Sex and the City, which was more mature, it was always very clear that the Gossip Girl characters were young people excited to party. Also: I had forgotten that a bandage dress could look so cute.
Private School Chic
Truly, one of the more long-lasting legacies of the show was its popularization of "couture prep." It screamed "Upper East Side private school" but also looked deeply cool: usually consisting of plaid, checks, or stripes, the designers went wild with the accessories and (as we saw here) tights and socks.
Over the Knee
The show didn't shy away from trendy outfits—on the contrary, they leaned in on current clothing, particularly with Serena. Those snake skin over-the-knee boots were a trend that holds up even today, particularly when paired with a more classic coat shape.
Great Green
Gossip Girl costume designers worked hard to put their characters in complementary colors, particularly those relationships we were meant to root for. Fascinatingly, Chuck and Blair were in different colored outfits, but the presents they got for each other were the matching element.
Boho
Serena in her natural element was much more relaxed. The golden hair, the big bag and chunky jewelry, the loose and flowy clothes. It felt like a trendier Sienna Miller in the best possible way. (I had questions about the furry vest, but it's a tiny nit to pick.)
Patterned Prettiness
Avid viewers of Gossip Girl—and there were many of us—would often enter into discussions of whether we were a Blair or a Serena. I was wholeheartedly a Blair; while Serena's outfits were more current for the time, the mix of Blair's posh side (the tweed jacket) and modern sensibilities (those platforms) was my definition of perfect.
Fishnets and Heels
Jenny went from Dan's sweet younger sister to an absolute fashion force in the span of a couple years. Case in point! When she broke out her beloved fishnets and put on a red lipstick, it felt like the "real" Jenny Humphrey was finally born. And she was stylish.
Matchy Match
It was always fun to witness BFFs Serena and Blair on screen together. It would always be obvious that 1) they were extremely different, and 2) they "got" each other in ways that no one else could. Here, the contrasting jackets laid all that groundwork without saying a word.
Pattern Mixing
It often felt like Blair got the most creative and typically "high fashion" outfits, which is probably why I loved her style so much. The contrasting striped blazer and checked coat was exactly what I wanted to look like in the late '00s. And points for her signature handband, as well.
New York Preppy
Like other slides on this list, the beauty of these outfits was in the similarity. Dan and Serena, as friends and off-and-on partners, looked perfect standing next to each other. Serena's camel coat and Dan's bag matched. His jacket and her shoes matched. They matched, literally and figuratively.
Frivolous Headwear
While Blair's headbands (often by Jennifer Behr) were the focal point of many of her outfits, the costume designers played with her headgear from time to time. This fascinator, which looks like a tiny mini-hat, was a nice variation on a theme. And that tonal look was great, to boot.
Mustard
More variation on a theme: Blair's mustard yellow beret hat. What might look silly on others looked perfect on her, thanks to the complementary mustard bow top and matching clutch. It's called maximalist fashion, and Blair was its undisputed queen.
Bubble Hem
The show really, really did its best work with event-wear. When the various characters had a wedding/party/Hamptons get-together to attend, the costume designers broke out gorgeous gowns. That pin floral bubble hem dress wouldn't look out of place today.
Perfect Contrast
While Blair went through (it could be argued) a less extreme style evolution over the course of the show, she still grew through her fashion. Over time, her looks became cooler and more inventive, including patterning mixing like this. Viewers saw her go from preppy teen to more mature young adult.
On the Steps
The steps of the Met were blessed with some of the best Gossip Girl outfits. The individual pieces of this look were really quite simple, but the genius was in the details. Blair's shoes matched Serena's vest over layer, and the two girls had similarly textured bags.
Going Green
While color-blocking to this degree might feel a little of its time, this still had a spark of inventiveness. A more modern iteration might swap the light green Louboutin platforms with a black pump, but the near match in color between the coat and bag was gorgeous.
Cruel Chic
Attention must be given to the wardrobe of Georgina Sparks, played by the late, great Michelle Trachtenberg. As befitting the wild, rebellious, sometimes malicious character, Georgina favored a more dramatic style. Those sunglasses were absolute perfection.
In the Details
I loved Jenny's later, edgier style, and it felt more authentic to the person playing her. But even in the earlier years (this photo was snapped in 2009), the seeds of that evolution were there. The eclectic mix of colors and patterns, plus a dash of surprise in the socks, meant that she was always one to watch.
Red Accents
Starting at the red, peep-toe Tory Burch flats, this outfit was perfectly representative of Blair. There was the nod to prep school in the skirt (let's be honest, the characters never wore a "uniform"), and then there were all the fashion grace notes: cardigan, bag, and (obviously) headband.
Most Formal
The more formal the event, the cooler the outfit on Gossip Girl. The dress under this coat was all sparkles with a little sheer on top, but the coat elevated the look even further. If you look closely, it seems that the detailing in the body was, in fact, safety pins!
Wedding Guest Perfection
On the occasion of Lily marrying Bart Bass, Serena wore a yellow Ralph Lauren dress from their Spring 2008 collection. It was giving off "bridesmaid chic" but also "best-dressed wedding guest" in a way that only Serena could pull off. And the gloves kept it from being too twee!
The Bride
There were a few weddings on Gossip Girl, which gave the designers ample opportunity to break out bridal couture. While Serena's gold-dipped gown was stunning, Blair took the cake with her two(!) gowns: this Vera Wang, which she wore to marry Prince Louis, and a blue Elie Saab to wed Chuck Bass.
