25 Outfits From the Original 'Gossip Girl' Worth Recreating

While the Gossip Girl reboot has fans abuzz for many reasons, the fashion of the original cast will always be a source of style inspiration.

If you're one of the millions of people watching HBO Max's Gossip Girl reboot, you may have felt inspired recently to rewatch the original. While the fashion in the new version is undoubtedly chic, there's something about the campy 2000s style of the original characters that just can't be topped.

From Chuck’s ascot ties to Serena’s thigh-high stiletto boots and even Little J's goth girl ensembles—all of which were paired with headbands pre-approved by Blair Waldorf, obviously—costume designer Eric Daman ensured each character had their own signature style. Daman took on the role following a successful run working with Patricia Field on Sex and The City (and was later responsible for outfitting The Carrie Diaries), and elevated the city-dwelling teens to that of Carrie Bradshaw and company, thereby cementing Gossip Girl’s place in pop culture. Now, Daman has returned to the world of Constance Billiard and St. Jude's to lead the wardrobe on the HBO Max reboot, ensuring that the new generation of Upper East Siders continues that legacy of major fashion moments.

As fans continue to enjoy Season 2 of the Gossip Girl reboot, let's look back on some of the most iconic looks from the original series.

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In the show’s opening scene in Grand Central Station, Serena sports the first of many simple, but sophisticated looks. This one consists of a breton-striped tee, light leather jacket, and matching brown neck kerchief.

A quintessential Queen B ensemble, Blair layers pinstripes and plaid over her Constance Billard uniform for a positively polished schoolgirl look.

The ladies’ fashion may have been the star of the show, but Chuck Bass' distinct personal style and many scarves deserve some praise, too.

The most innocent of Jenny Humphrey's (Taylor Momsen) ever-changing personas, she stands poised in a fully prepped out Constance uniform.

In her angsty teen phase, Jenny goes grunge in a groutfit.

Before corsets became a mainstream trend, Blair lounged in her lingerie set.

Georgina Sparks (Michelle Trachtenberg) was no one's favorite character, and frankly this chaotic assembly of Uggs, stockings, and glitter helps to understand why.

This silver dress successfully sabotages Vanessa by being utterly see through, but before her naked dress moment, she rocks this sparkly one shouldered gown.

Serving major Mary Quant-inspired vibes, Chuck and Blair's boldly colored school day accessories steal this Constance courtyard scene.

Serena dashes through Manhattan in snakeskin pumps and a standout Burberry trench coat.

You're not doing summer in The Hamptons right if you aren't toting a wicker basket mini bag next to your bestie clutching Chanel.

Blair’s ice skating look is perfectly coordinated with a plaid cape and skirt, topped with a matching beret style cap.

Serena and Blair twin in backless Abigail Lorick sheath dresses, because matching with your bestie never goes out of style.

Jenny makes an impossibly short H&M mini dress look high fashion at her Season 2 guerrilla fashion show.

For a dramatic Studio 54-themed party, Serena goes for a jaw dropping gold lamé Diane von Furstenberg dress.

Out for a stroll, Blair dons a pattern heavy Moschino bubble dress and Serena a caged Georges Chakara V-neck.

Blair’s red Oscar de la Renta gown brings the drama to a Paris episode.

Vanessa is the queen of pattern mixing and making chunky accessories look chic.

Blair à la "Rosemary's Baby," in a Marc Jacobs babydoll dress.

Whether Chuck's behavior reflects that of a gentleman is debatable, however he was always dressed like one and this red ascot tucked into a velvet smoking jacket and silver silk cravat are a prime example.

They may have been the bad guys in this episode, but Juliet Sharp (Katie Cassidy) in this J. Mendel ruched tulle gown and Vanessa in her floral chiffon Christian Cota dress still looked damn good.

Lier, thief, criminal...Say what you will about Ivy Dickens (Kaylee DeFer), she looks stunning in this Badgley Mischka Fall/Winter 2011 gown.

Vanessa's most show-stopping look is this Reem Acra princess gown.

Serena attends the NYC Ballet in a sheer but elegant Zuhair Murad floor-length dress with a grey chiffon train.

An unconventional color choice for an unconventional couple, there is no forgetting Blair's Ellie Saab wedding gown.