Close your eyes and picture this scene: It’s September 19, 2007, at approximately 9 p.m. Where are you? What are you doing? Who are you with?
If you were a 20-something college student like Tyler McCall, Casey Lewis, and me, odds are you were sitting on the couch with your roommates and tuning in to the series premiere of Gossip Girl on The CW. Back when must-see TV was actually a thing you had to pencil into your schedule, it didn’t take long for the highly anticipated adaptation of the young-adult book series by Cecily von Ziegesar to earn a spot in our lineup of weekly shows.
Looking back at what was arguably among the last cohort of non-streaming TV sensations (Gossip Girl counts both Mad Men and Breaking Bad as contemporaries) offers not only the welcome respite of nostalgia but also an amusing glimpse into the now-questionable costumes, personal style, and fashion statements of our beloved Upper East Siders. (I don’t know about you, but I never want to see another bubble hem again!)
As the IRL minions of Blair Waldorf, Serena van der Woodsen, and the rest of the Constance Billard School for Girls gang, it’s hardly a surprise that McCall, Lewis, and I all went on to not only pursue careers in fashion media but also spent time at digital editors at Teen Vogue. While you are likely familiar with McCall for her current role as editor in chief of Fashionista, you might also know and love her as the mind behind #WaldorfWednesdays on Instagram. Similarly, while Lewis is an editor at New York Magazine by day, she spends her leisure time curating @ThankYouAtoosa, the delightful throwback account in which she chronicles the hits (and misses) of teen magazine culture from the ’90s to 2010s.
And who am I? That’s one secret I’ll never tell.
Just kidding. Like Little J, I tend to lurk a bit more on the fringes as the content strategy director here at Who What Wear, but I low-key wrote a master’s thesis on the evolution of female characters on television—no joke. If that doesn’t make us some of the most qualified Gossip Girl fans out there, then, by all means, please introduce me to our new queen bee.
So while prep school uniforms and empire waists may not be making a comeback in our closets anytime soon, it’s safe to say that The Met steps will always hold a special place in our hearts. Now, without further ado, below are nine of our favorite Gossip Girl outfits with a bit about why we loved them.
Prep School Perfection
"I always loved Blair and Serena's everyday school outfits way more than their gala gowns or super fashiony, extremely Eric Daman-y looks. I grew up desperately wishing I wore a school uniform, and even though real school uniforms looked nothing like the ones on Gossip Girl, I obsessed over their poufy, pleated skirts and crisp button-downs. I would have been laughed right out of my high school if I showed up in knee-high socks and flats, but man, Blair and Serena made it look cool." — Lewis
"When it came to the school uniforms, the show really hit its stride in season two. Did they push the boundaries of what might pass the dress code at an elite private school in Manhattan? Sure. Did Blair know how to kill it in a cape? Absolutely. And what, you didn't wear a bejeweled headband to school? Okay. (I found this exact headband by Jennifer Behr in the corner of her sample sale, and I have never been prouder of my shopping prowess.)" — McCall
"I'll be honest: I went to a prep school where my classmates and I looked nothing like this, ever. Our dress code of collared shirts, blazers, and chinos was decidedly masculine (the school transitioned from all boys to co-ed in the '70s but neglected to consider female bodies in the dress code until at least 2010), so seeing Blair and Serena on screen gave me a glimpse of what might have been. That said, white button-down shirts are still a staple in my wardrobe, so thank you, Ralph Lauren." — Elovitz
"Season one, in my opinion, was as good as it got as far as Gossip Girl fashion went. How flawless were these dresses? I remember reading about Abigail Lorick in Teen Vogue—if my memory serves before Gossip Girl came out—and I just thought she was the coolest. I think Eleanor Waldorf's fictitious fashion line was based on Lorick, and in my mind, the designer (a former Ford model) was basically another character on Gossip Girl because her clothes were so Blair Waldorf. She may have even made a cameo on the show?" — Lewis
"The jumping-off point of inspiration for Serena was Kate Moss, which meant over-the-knee boots became something of a staple for her. I have doubts about whether these would fly at a real private school, but they still look incredible. I always was more of a Blair than a Serena, but that never stopped me from desperately wanting a pair of Stuart Weitzman's iconic thigh-high boots." — McCall
"My hands-down, all-time-favorite look from Gossip Girl is Blair's outfit from the first Thanksgiving episode, "Blair Waldorf Must Pie." First, it must be said that this is the best episode of GG. Second, it's just quintessential Blair, from the lacy Marc by Marc Jacobs dress to the bow-patterned tights. I bought a similar pair from Forever21 at the time and wore them to death. Maybe that's why I still can't get enough of a novelty tight?" — McCall
"I spent several years wearing empire-waist, babydoll dresses and patterned tights because Blair Waldorf did. Both things looked truly awful on me, but they were made for Blair. I still dream about her lace Marc Jacobs dress on the perfectly named season one Thanksgiving episode, "Blair Waldorf Must Pie!” The Trina Turk capelet is really quite ugly, but it's so, so 2007, and that makes me love it." — Lewis
"Because Gossip Girl always started around the same time school came back into session, we never saw very many summery looks on the show, which was a shame. But when we did—like on season two's debut episode, "Summer, Kind of Wonderful," costume designer Eric Daman knocked it out of the park. I'm still obsessed with Blair's look from the white party, a scalloped Marc by Marc Jacobs dress and a floral Jennifer Behr headband. So dreamy." — McCall
"Spoiler alert: I fell more in love with Blair's (second) wedding dress than she did with the man she was going to marry in the series finale. I don't know if it was the conclusion of my favorite show that was giving me all the feels or what (hey, it certainly wasn't her groom), but if I had a secret wedding Pinterest board, this Elie Saab Couture 2012 gown in baby blue would be the only thing on it." — Elovitz
"'Iconic' is a bit overused at this point, but there's no other way to describe Serena's very first outfit on Gossip Girl's pilot episode. The striped Petit Bateau shirt, the leather blazer in the most perfect shade of camel, the little pop of yellow in the form of the handkerchief. I can't think of another time she dressed so understated, but it suits her so well." — Lewis
"Unsurprisingly, I related to Jenny's wardrobe most when she was doing her best Blair Waldorf impersonation toward the end of the first season. There were lots of pastel shades and darling socks. Sure, she would become a bleach-blonde goth in just a few short years, but we'll always have the memories of sweet Little J." — McCall
"How could we skip the legendary Chuck Bass scarf? Chuck's style went off the rails by the end of the show (remember the time he was dressed like Prince George?), but early on, his preppy Upper East Side uniform worked so well for him, and the J. Press scarf looked so good with all of his popped collars and fancy layers." — Lewis
"Like many of my fellow Gossip Girl fans, while we may have aspired to be a Blair or Serena, it was often easiest to relate to Jenny Humphrey. I don't know that it could be called a glow-up, but to say that Little J went through a serious style evolution during the series's six seasons would be a major understatement. As Tyler points out, Jenny started off by emulating Blair's style, then gradually embraced her Brooklyn-bad-girl side as the show progressed. Jenny traded in her preppy headbands, bows, and bright colors for layers upon layers of black eyeliner, offbeat accessories, and an essential leather jacket. While Jenny's anti-establishment new persona lost me along the way (let's face it: you live in a loft in Dumbo, dear), I'll always appreciate how the changes in her character's costumed reflected her growing confidence as an individual." — Elovitz
Drew Elovitz is originally from Pittsburgh, Pennsylvania, but has spent the last decade living and working in New York City. She earned a master's degree in media and popular culture from New York University, then began her career on the internet as the Twitter voice of Barbie. She worked previously at Who What Wear as the director of content strategy and also spent several years leading the social media teams at Teen Vogue and Entertainment Weekly. You'll find her byline on the site around topics such as celebrity fashion, must-have basics, beauty favorites (particularly nail polish), and wellness tips and tricks. Her personal style tends to favor the classics: She loves crisp white button-downs, sneakers, and skinny jeans—and no look is complete without a great pair of oversize sunglasses and a trusty leather jacket. After she finishes reading the entire internet every day, she can be found dining out at her favorite restaurants, trying new beauty treatments, or indulging her historical-fiction habit.
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