A Look Back at Gossip Girl's Finest Fashion Moments

A Look Back at Gossip Girl's Finest Fashion Moments
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A Look Back at Gossip Girl's Finest Fashion Moments

Blair’s Headbands

Before Blair Waldorf, the wearing of headbands and hair bows was generally reserved for the six-and-under set. But the first season of Gossip Girl totally changed all that forever–or at least a couple of seasons, anyway. Fine, so Leighton Meester was technically playing the role of a high school student–but her character managed to make childlike hair adornments totally appropriate for us adult-folk. She had a different one for every outfit: They were sweet without being obnoxious and suited the role to a tee.

I don’t care what any American Apparel-hoarding, Williamsburg-dwelling hipster tells you: Those hair bows you’re wearing were made possible by the one, the only…Blair Waldorf.

Bright Tights

Pre-Gossip Girl, I was aware of only three colors of stockings and whom exactly they applied to: Black was for grown-ups, white was for children, and sheer nylons were for women with no taste (a valuable lesson I learned from Paris Hilton). I dreaded that time of year when the air got a little too cool for bare legs–but Gossip Girl changed all that. The girls of Constance, led by Queen B, treated their tights as accessories, often coordinating them with aformentioned headbands. Suddenly, I dreaded going bare-legged in the summer–my outfits all seemed so incomplete and, quite frankly, lame-o sans bright, matching tights.

Serena’s Inappropriate Outfits

As prim and adorable as Blair was with her matchy-matchy get-ups, Serena (Blake Lively) always managed to one-up her with a totally inappropriate outfit. I mean really, what exactly were the uniform regulations at Constance? Throw on a mini-kilt and a borrowed necktie from whichever guy you’d hooked up with the night before–knee socks optional? So it seemed for our Serena, anyway. She also mastered the art of inappropriate cleavage and micro hemlines, which she showcased whenever possible.

Whether it was a wedding, Thanksgiving, or just a midday stroll through the Upper East Side, any time was a good time for Serena to put her goods on display. And yet somehow, while Serena seemed to be permanently stuck in a state of underdress and/or walk-of-shame attire, she never once gets cat-called or harassed. Food for thought…

Dorota’s Festivewear

Blair’s housekeeper/partner in crime Dorota was the sassiest maid this side of Poland. True, most of the time, ‘Rota was resigned to wearing standard black and white maid-fare, topped off with a little hair doily. But every so often, she showed off her seasonal cheer with a little flare to compliment Miss Blair. Talk about making it werk at work.

Chuck’s Gladrags

That handsome mother Chucker. Chuck Bass (Ed Westwick, yum) had a lot going on in his life at all times–a rich, dead father (or was he?), a mother who died during childbirth (or did she?), his on-again/off-again love affair with Blair, and a name that made for the most creative puns on basic cable–all of which was eclipsed by his over-the-top extravagant wardrobe. The J.Crew catalogue has nothing on this “teen”‘s penchant for layering and mixing prints.

As his character evolved, so too did his masterful wardrobe: With Chuck’s inheritance of Bass Industries came a more sophisticated, GQ approach to dressing–suspenders, pea coats, seriously fancy socks, slim-fit dandy suits for days and a suave, slicked back ‘do. In real life, all of these factors combined would put Charles Bass in a constant sartorial face-off with the Brant Brothers for a spot on our weekly best dressed round-up–which wouldn’t be pretty. Actually though… it would be really, really pretty.

The Onscreen Gothification of Taylor Momsen

Our dear, sweet Little J. Recently, I decided to use my spare time in the wisest way I possibly could: By re-watching the entire series of Gossip Girl, beginning to nearly-end. And for lack of a better word, it was so weird seeing Taylor Momsen looking so… normal!

Whereas most actors and actresses resist switching up their look until after their contracts are up (see: Emma Watson post-HP), Momsen seemed to somehow convince the producers of GG that her character Jenny Humphrey should evolve into a raccoon-eyed neo-goth, just like the actress did in real life. And evolve she did, right back to her estranged mother’s house in Hudson (i.e. off the cast). It’s pretty remarkable to watch, really. Cindy Lou Who, we hardly knew ye.

Random Fash Pack Guest Spots

The list of fashion people who’ve made single episode appearances playing “herself/himself” on Gossip Girl has come to look like the VIP guest list for the next highly anticipated H&M collaboration fete.

Notables include: Tim Gunn, Tory Burch, Georgina Chapman, Polo model Nacho Figueras, Cynthia Rowley, Joe Zee, socialite Tinsley Mortimer, Isaac Mizrahi, Vera Wang, Karlie Kloss, Vogue‘s Meredith Melling-Burke, Hamish Bowles, Lou Doillon, Rachel Zoe, Tyra Banks, Diane Von Furstenberg, Hamish Bowles, Charlotte Ronson, and W editor Stefano Tonchi. Alexa Chung is slated to pop up in the sixth season. Of course, none of these names can compare to the star power of world-renowned designer and series regular Eleanor Waldorf, whose groundbreaking collections consistently blow us away each NYFW. Up-and-coming talent Jenny Humphrey also had a brief 87-episode stint on the show.

S & B’s Paris Wardrobe

In my totally unbiased opinion, the single best fashion moment in Gossip Girl history actually took place approximately 3,500 miles from the Upper East Side. The time: Season 4, episode 1. The place: Paris, France. After gallivanting in gay Paree, looking fab and forgetting their NYC boy trubs, Blair and Serena treated us all to a montage-y glimpse at how we wish we’d gotten to spend our summer: Namely, gallivanting in gay Paree whilst looking fab and forgetting our NYC boy trubs.

Enter, the best GG fash moment ever: B’s dreamy cherry print Moschino dress/beret combo was sweeter than any macaron from Ladurée, while S looked gorgeous and (as always) totally overdressed for daytime in a glittery caged Georges Chakra confection. Next time I fly abroad for the summer on my private jet, I’ll be sure to pack an endless supply of cash, couture, and of course, a CW cameraman to capture it all.

Designer Dresses

Wait, so the girls at your high school didn’t wear Marchesa to prom?

Gossip Girl stylist Eric Daman took total advantage of the characters’ unending affluence, thus turning each episode into a rousing game of designer ‘I Spy.’ Fresh-of-the-runway gowns had a good a chance of showing up on Gossip Girl as the red carpet.

A few favs? Serena’s gold Pamela Dennis cotillion gown (later worn by certified creeper Ivy) and the lacy gray Zuhair Murad she wore to the opera, as well as the yellow boobylicious Ralph Lauren number she donned for her mother’s wedding. As for Blair? You may recall a white Vera Wang dress she wore on the day she um became a PRINCESS, aka the more important royal wedding of the past decade.

Chace Crawford

Ok fine, so this has literally nothing to do with fashion. I’m just really going to miss seeing Chace Crawford lighting up the TV screen in my combined living room/kitchen area on the weekly. Nate always had the most throw-away love plots: Going out with him usually meant your contract was expiring–but on the upside, you got to make out with Chace Crawford before you were auf’d.

To make matters so much worse, Crawford has said that after Gossip Girl wraps, he’s planning on leaving New York. Which means I’ll have little to zero chance of ever running into/making out with him in real life. Someone get this guy a CW spin-off show, quick!


It's official: The series finale of Gossip Girl is a mere ten episodes away. While many a cynic may argue that the show actually ended sometime during the second season, for us die-hard Upper East Side wannabes, this news is harder hitting than a Nairtini to the head. Personally, Blair Waldorf is not only listed as an 'inspirational person' on my Facebook, but she's also my pet gerbil's namesake.

There's been a lot to love about Gossip Girl: The clever scheming, the ridiculous love triangles (hexagons?), the endless 'Chuck Bass' puns, the Williamsburg cityscapes, Blair's putdowns, the "underage" drinking, the predictable plot twists, Serena's endless supply of attractive man-suitors, and of course, Dorota. But of course, what we'll miss most of all is the fashion. Gossip Girl has been on top of the fashion game since its first "XOXO" way back in early 2007, and as the series progressed, the characters' signature styles arguably surpassed the plot development in terms of critical praise.

Between Blair's preppy headbands, Chuck's dandy suits, and Serena's gravity-defying cleavage, the influence the kids of Constance have had on street style and fashion spreads alike is undeniable. So, as a tearful ode to our favorite CW soap, here's a look back at some of the style stand-outs that have made the last five years of impossible-to-follow plot lines a little more bearable.

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Photo Credit: Courtesy of CW

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