The Gossip Girl Style Guide: How To Get The Best Looks Of Gossip Girl’s Queen Bees

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Hey upper East Siders, this just in: A new class is officially in session at Constance Billard via HBO Max, and to celebrate, I’m breaking down some of the best outfits from Gossip Girl. 

It’s been almost 14 years since the CW first introduced us to Manhattan’s elite, and I know I’m not the only one still trying to recreate Blair Waldorf’s most iconic looks. To this day, the show’s fandom mimics that of Sex and the City of which loyal watchers define themselves based on a character’s style persona. But whether you identify as a Blair or a Serena, costume designer Eric Daman made sure each character’s aesthetic was as covetable as it was distinguishable. 

S&TC served us plenty of labels, and Gossip Girl was no different. Once the show gained traction, designers from Chanel to Chloé, Balmain to Marc Jacobs, and numerous other names wanted a cameo, and viewers wanted to shop the looks. Unfortunately, not all of us are billionaires with unlimited credit; replicating the best outfits on Gossip Girl takes a little creativity and a lot of poking around the internet. To save yourself hours of online sleuthing, I’ve done most of the grunt work for you. Read on to find out how you can dress like S and B, as well as Constance Billard’s newest teen royalty, Julien Calloway and Audrey Hope.

Blair Waldorf: The Little Black Lace Dress

Headbands. That’s it. That’s the style guide. 

I’m kidding. (Sort of.)

There are two key pillars to dressing like Blair Waldorf: Leggings are not pants and headbands are gospel. We see these style rules put into practice from the show’s pilot. Blair wears an all-black ensemble: a so-called “Waldorf design” that’s actually a lace mini dress by Anna Sui, matching tights, and a rose-detail headband to match. 

While the Anna Sui dress is long sold-out (keep in mind, timeless as this particular number may be, the pilot did first run in 2007), this 3/4-Sleeve Heavy Lace Dress from Dolce & Gabbana comes stunningly close. If you’re on a budget, however, ASTR the Label’s Leilani Mini Dress is of a similar style (for a fraction of the price).  

As for Blair’s signature headpiece, Jennifer Behr was a go-to for costume designer Eric Daman. The Black Triple Rosette Headband is pricey but worth the splurge. For a more affordable alternative, the Black Rose Flower Headband from Brittsblossoms or Madewell’s Skinny Puffy Braided Headband would be equally as chic.  

Serena Van Der Woodsen: Shopping In Salmon

Nine out of 10 times, Serena’s boho-chic aesthetic is more attainable and down to earth than Blair Waldorf’s wardrobe. Really, their styles couldn’t be more different: Blair is a perfectionist and likes everything to match; Serena isn’t afraid to mix patterns and textures. B’s signature is a headpiece; S’s signature is footwear - girlfriend loves herself a pair of heels. 

One of Serena’s most iconic looks, in my opinion, is this trouser-and-tank combo from the first episode of season 4, in which Serena and Blair take on the Parisian shopping scene. The outfit is simultaneously comfy-casual and highly fashionable: bright salmon bottoms by Suno, a beige tank from Stella McCartney, chunky snakeskin belt, turquoise statement necklace, Zadig & Voltaire hat, and a pair of rafia oxfords by Dries van Noten. 

The look is almost too easy to mimic these days, as trousers are the comfy pants rising to popularity in light of re-entering society post-pandemic. You can find similar styles from Hebe Studio and Essentiel Antwerp. Pair the wide-legged bottoms with a loose-fitting, beige, or cream tank like this one from M.M. La Fleur, and accessorize with this belt and this necklace from Sezane. To really complete the look, Serena’s feather-trilled wool fedora hat is available for $105 on TheRealReal. 

Julien Calloway: A Button Up Dressed Down

Costume designer Eric Daman has his new class of prep school girls reinventing the uniform Gen Z-style, and Julien Calloway’s Met steps ensemble is exactly what I had in mind for a modern Constance Billard queen bee. Sure, the reimagined look may not include headbands, but there’s no denying Calloway is becoming a fashion icon in her own right.

What I love about Calloway is that her style combines elements of both Blair and Serena, but it’s true to the new persona’s unique flare: It’s preppy, laid back, and marries masculine and feminine pieces. With its loose-hanging tie and untucked, oversized button-down, this look could be described as intentional just-rolled-out-of-bed chic. 

To mirror the look, I’d pair the Lioness The Carrie Button-Down Shirt Dress and Rowing Blazers’ US Rowing Silk Necktie with the ASOS DESIGN pleated mini skirt in navy. For footwear, Calloway dons the Maryana Tall Boot from Schutz, and lucky us, they’re still available for purchase.

Audrey Hope: Sailor Chic

If there were any style persona I was going to resonate with from the reboot, it was that of Audrey Hope, aka the modern-day Blair Waldorf. Growing up the daughter of a fashion mogul, Hope was destined to have some highly fashionable taste, and it shows through her outfits. But while she has a few striking parallels to Blair (who, if you remember, also had a wildly successful fashionista for a mother) Hope’s outfits feel slightly more attainable. Her twist on the prep girl uniform is also the quintessential back-to-school fall wardrobe, an aesthetic I aspire to channel every autumn. 

While I’m partial to Hope’s chunky sweater and tights collection, this nautical ensemble demands highlighting. Her sailor pants are Derek Lam and cost a whopping $385 ($365 if you opt for the cropped version), but the Saint + Sofia Chelsea Pant makes for an almost identical dupe. For top options, I narrowed it down to two: This Striped Piqué Tank from Toy Sport or this cotton short-sleeve polo shirt from Moncler as preppy as they’re both equally as preppy as Hope’s polo tee.
From 2007 through 2012, the original Gossip Girl series supplied us with plenty of outfit inspiration, across many different stylistic tastes and transformations (remember when little Jenny Humphrey went from prep to punk?). With its reboot comes new outfits inspired by a whole new generation of fashionistas, and I can’t wait to see what looks the new class serves up in coming seasons. I have no doubt there will be something for everyone to love, covet, and shop.

From 2007 through 2012, the original Gossip Girl series supplied us with plenty of outfit inspiration, across many different stylistic tastes and transformations (remember when little Jenny Humphrey went from prep to punk?). With its reboot comes new outfits inspired by a whole new generation of fashionistas, and I can’t wait to see what looks the new class serves up in coming seasons. I have no doubt there will be something for everyone to love, covet, and shop.