While it might not be the case these days, there was a time when heels reigned supreme, when headbands were en vogue when necklaces were large and dresses and skirts were preppy. That time is encapsulated in the looks from Gossip Girl, the svelte Upper East Side of New York-set drama that aired on the CW between 2007 and 2012.
While Leighton Meester’s Blair Waldorf was the most popular dresser of the bunch, over the course of six seasons, a lot of the celebrity fashion worn in the show were outfits that were way ahead of their time or timeless and it was devastating when Gossip Girl ended and we had to say goodbye to the looks. Without further ado, here’s some great ones that still hold up.
Blair Waldorf’s Black Opening Episode Dress (Season 1, Episode 1)
Gossip Girl first introduces us to Blair at a party with her mother. She’s allegedly wearing one of Eleanor’s designs, but it's actually a sweet Ann Sui look that was ahead of its time. Plus, black has always and will always hold up. You know you love it.
Serena’s Very Best Gold Dress (Season 5, Episode 9)
While Serena van der Woodsen wears a lot of gold and yellow throughout Gossip Girl, hands down her best number was in Season 5, Episode 9 when she rocks a gold, vintage-looking Diane Von Furstenberg dress. Her teased hair really amps her look up even more.
Chuck Bass' Bejeweled Formal Look (Season 2, Episode 12)
While the ladies of Gossip Girl get most of the notice, we'd be remiss if Chuck Bass didn't make this list at least a few times. Of all the men on the show, Bass has a personal sense of style that is memorable without being tacky. This jacket from Season 2 is probably the best example of how standout his formalwear really was.
Vanessa's Gorgeous Twist Front Dress (Season 3, Episode 5)
There was no shortage of gorgeous ball gowns worn during Gossip Girl's six-season run, but my favorite of all of them was the ballgown worn by Jessica Szohr in Season 3 during an Old Hollywood dream sequence Blair has. Wildly, Vanessa is one of my least favorite dressers on the series, but this Reem Acra look is still fire and would fit so many body types.
Serena Van Der Woodsen's Flared Pink Pants (Season 4, Episode 1)
A tailored pant is a girl's best friend, and this lovely look from Serena van der Woodsen combines my two favorite things: comfort and Barbiecore fashion. Pants like these have made a resurgence, but they'll never not be a classic look.
Blair Waldorf's First Wedding Dress (Season 5, Episode 13)
Of all the iconic outfits from the series, the most standout and memorable seemingly has to go to Blair's white wedding dress. The lace overlay and pretty bow in front give the dress an extra edge, but it's certainly a situation where the real party is in the back. This storyline didn't end so hot, but the dress is still a stunner.
Serena Van Der Woodsen's Caged Dress (Season 4, Episode 1)
There are a slew of outfits shown from Blair and Serena's time in France thanks to a killer montage at the beginning of Season 4, and all of them are top notch. I still want this cage corset dress from George Chakra couture that's covered in Swarovski crystals. Because Swarovski crystals will always make everything better.
Blair's Floral Dress (Season 4, Episode 1)
Want to know what to wear to a museum? Try a floral chiffon number like the one Blair Waldorf rocks that is flowy and ahead of its time. Particularly given she wore it with a notable and gorgeous pearl choker that will always be a work of art.
Jenny Humphrey's Goth Girl Meets Prep (Season 2, Episode 14)
Part of the fun of early episodes of Gossip Girl happens when the ladies level up the school uniform look. Jenny's got her crossover tie on with a black peacoat here, but the really chic look is the pink tulle under her plaid skirt coupled with a pair of timeless boots. It's school girl up top and punk rock on bottom.
Redemption For Vanessa’s Snowflake Ball Dress (Season 2, Episode 12)
I love the rope detailing in the shoulder of Vanessa’s dress from Season 2's Snowflake Ball. If you’ve seen the series, you know the dress would ultimately be ridiculed by pretty much everyone after a light revealed it to be made of thinner material than expected, but as we all know, Vanessa's sheer take on fashion would be right on trend years later. It helps the simple silhouette could fit in any time and place, too.
Chuck Bass In His Gordon Gekko Era (Season 3, Episode 1)
Chuck Bass never shied away from color during Gossip Girl, but his suspendered Gordon Gekko era in Season 3 is really when his fashion takes a step forward. Intriguingly the '80s vibes may have come from Mr. Bass wanting to emanate his dad when he took over his company, but it's certainly a look he owns.
Blair's Famous Photoshoot Dress (Season 1, Episode 4)
Serena and Blair frequently have a friendship rife with tension, but in Season 1 things are particularly awkward. You can see the foundations of the friendship during Episode 4, in which Serena pitches Blair for a photoshoot for her mom Eleanor's fashion brand, then helps Blair to have fun in the gorgeous black and yellow floral dress so the pictures come out great.
Nate Archibald Untucked, Untied And A Little Askew (All Seasons)
Outside of Nate Archibald wearing fine quality clothing, there isn't a ton to remark about his look. Except he nearly always wears it a bit askew. Tie undone, shirt untucked, a couple of buttons loose at the top. The look's a keeper, but perhaps none is better than the loose tie with the school uniform.
Lily's Strong-Shouldered Black Dress (Season 4, Episode 18)
An RM by Roland Mouret special, this gorgeous black look worn by Serena's mother is one of many black dresses she wore during the run of the show. They're all elegant, but the way this dress is tailored makes it standout no matter what year we're living in.
Serena's Sparkly Mini Skirt And Sweater Combo (Season 5, Episode 12)
One thing Serena does well that not everyone can pull off is mix patterns and prints. Some of her outfits are really out there, and some of them stand out in the perfect way, like her sequined mini skirt and sequined sweater paired with a neutral black coat and brown bag in Season 5. I'd still wear this (though maybe with a flat shoe).
Blair's Sparkly Dress And Headband (Season 6, Episode 5)
There's no dearth of beautiful ballgowns in Gossip Girl, but this sparkly floor-length look kicks things up a notch via its bold accessories. That headband! Those startling earrings! This was the era of extra, and Blair wears it well.
Lily Dives Into Prints! (Season 5, Episode 4)
Satins and the color black are what Lily favors the majority of the time, but every now and again she'll dive into print and color in a satisfying way and this is one of my favorite examples. The white earrings with the yellow pop add the perfect extra touch.
Blair's Colored Tights (Many Eps, But This One's Season 1, Episode 15)
Rocking red tights with a bright yellow coat from Ralph Lauren should not work, but pairing it with a cute, preppy collared blouse and a neutral bag really made Blair Waldorf pop. Colored tights should always be a wardrobe staple, though I recognize they come in and out.
Jenny Embraces The Dark Side (Season 3, Episode 4)
Jenny wears a lot of black when she starts coming into her own at Constance Billiard in Season 3, but this bubble skirt and black jacket combo is among my favorites. If she'd thrown in her signature fishnets it would have been perfect.
Georgina Rocks A Purple Dress (Season 2, Episode 23)
Georgina was typically seen in signature black and other dark tones, but appearing in Season 2, she wore a sweet textured purple dress with a chain at her belly. The hardware is a nice touch and helps the dress to stand out as something a little different.
Serena's Grey Coat And Cashmere Gloves (Season 3, Episode 13)
Early on, most of the coats we see Serena in are leather, but by Season 3 she's playing around with her look a bit more. This is one of the rare times we see Serena in more of a neutral, pastel palette and it looks great on her.
Dan And Serena At Blair's Wedding (Season 5, Episode 13)
This one's really a two-fer and it's mostly because this gossamer look is perfect for Serena and one of the rare occasions Dan is fully dressed to the nines. A three-piece suit for Dan! Headwear for Serena! The best part for me though is that you could see either of these looks at a wedding today and they'd still be posh.
Jenny's Goth Formalwear (Season 3, Episode 9)
I know people love early seasons, but I'm kind of starting to feel like Season 3 may have been peak Gossip Girl fashion, as this formalwear look from Jenny with the puffed out skirt and red lip is so pretty and edgy at the same time. It helps she has Nate Archibald as an accessory too.
Blair's Finale Wedding Dress (Season 6, Episode 10)
A lot of fans are partial to Serena's gold dress in the Gossip Girl finale, but I've always loved Blair's ice queen dress more. And the headband! It's sort of giving Downton Abbey and I'll forever love that Leighton Meester's character ended on this note.
Juliet Goes Gossamer (Season 4, Episode 8)
Most of the best looks on Gossip Girl decidedly don't go to the b-tier characters, but this look from Juliet trumps both Blair and Serena's look in the same scene. (Blair has a kind of cool backless halter dress on, but it's nothing special, and Serena's beaded number feels like it ages her up quite a bit.) Katie Cassidy's gossamer dress is timeless and I still think about the asymmetrical hemline.
Serena's Yale Outfit (Season 2, Episode 6)
Serena does casual better than anyone else on Gossip Girl (my apologies to Vanessa, who is casual more often). Probably because she's so upscale without seeming to be trying. I've never seen a blazer as unique as the one she wore to the Yale campus in Season 2. She paired the look with jeans and the perfect bag and riding boots. Want.
Blair's Green Dress Season 5, Episode 1
I've always kind of felt Blair's green dress in the opening episode of Season 5 is a showstopper that doesn't get enough time to shine. I don't see people talk about it much, probably because Serena's California storyline takes over in the episode, but I still think it's a showstopper.
Ivy's Flapper Dress (Season 5, Episode 7)
Ivy wears a lot of flowy outfits that look dated years later, but on the night of the masked event she pulls out all the stops in a sparkly flapper dress with floral detailing on the lower half. The silhouette won't work for everyone, but it sure is stunning to look at.
Chuck's Animal Print Collar (Season 5, Episode 12)
One of Chuck's more subtle-yet-unusual looks came in Season 5. He traipsed around the streets of New York in what at first glance seems to be a pretty demure grey suit with a semi-unexpected brown vest with it. But if you look at the collar of his suit coat, you'll see Chuck Bass at his finest: animal print.
Diana's Yellow Dress (Season 5, Episode 4)
Before this moment, I would have argued Serena is the queen of the yellow dress. But Liz Hurley's brief foray into the world of Gossip Girl is full of fitted sheath looks that still look on trend. This one's a keeper.
Serena's Marilyn Monroe Nod (Season 5. Episode 13)
Lots of people have nodded at Marilyn Monroe's famous dress from Gentlemen Prefer Blondes, including Margot Robbie channeling Monroe as Harley Quinn. But something about Blake Lively in the look feels like real theater, in a good way. It's timeless, pink, and best of all, dripping with jewels.
Jenny's Marchesa Moment (Season 3, Episode 20)
Little Jenny Humphrey mostly attempted a punk rock or at least edgy look during the course of the show, but somehow she made a mint number from Marchesa look cool before her big child star exit form Hollywood. The brand was popular during the show's run, and while it's less popular today, I still wouldn't be mad if I had this on a hanger.
