Gossip Girl Reboot vs OG Gossip Girl: How Does the Fashion Compare?

In the Gossip Girl heyday, the show’s hyper-posh Upper East Side costuming made the style mood board of millennials’ collective consciousness (at least of those who watched the show.) In 2007, it was Blair Waldorf and her accompanying clique who defined what preppy style meant. Jenny Humphrey outlined to us edgy for the modern teen. Gossip Girl’s thesis on personal style showed itself in the ever-changing style modifications to their high school uniforms (was that even allowed?) Now, a new generation will have a new Gossip Girl of their own, but how will the fashion compare?

It doesn’t matter whether or not teenagers watching the show and were actually dressing like its main characters. (Honestly, we hope most weren’t). Even if the fashion in Gossip Girl existed solely as a glossy aspiration, the original show’s social influence on adolescent style was undeniable — a quick eBay search still has pages and pages of listings labeled “as seen on Gossip Girl” — so the upcoming Gossip Girl reboot has big shoes to fill.

The reboot is slated to premiere on HBO Max in 2021 and though we have yet to see much of the new Gossip Girl save for a slew of on-set images, it appears the tradition among the boys of St. Jude’s and the girls of Constance Billard to alter their uniforms to suit their personal tastes is going nowhere. (OG costume director Eric Daman is on also board this time, after all!)

The signature forest green plaid remains, but the new cast seems to be trading stockings for bike shorts under anything oversized. One of the early photos from the shootings in NYC shows actor Whitney Peak sitting on the steps of The Met wearing her plaid pinafore dress uniform with tube socks, Adidas Superstars, and repping a red tote bag from Revolution Books, a leftist New York bookstore. 

Whitney Peak seen filming for “Gossip Girl” outside the Metropolitan Museum of Art in the Upper East Side on November 10, 2020.Gotham
Leighton Meester and Blake Lively on location for “Gossip Girl” on March 14, 2008 in New York City. James Devaney
Whitney Peak on November 10, 2020 in New York City.Jose Perez/Bauer-Griffin
Jordan Alexander and Whitney Peak are seen at the film set of the “Gossip Girl” on November 10, 2020.Jose Perez/Bauer-Griffin
Leighton Meester and Blake Lively on location during a filming of ”Gossip Girl” on March 14, 2008 in New York City. Arnaldo Magnani/Getty Images
Leighton Meester and Blake Lively during season one of “Gossip Girl” in 2007.©CW Network/Courtesy Everett Collection
©CW Network/Courtesy Everett Collection
Jose Perez/Bauer-Griffin

In the original series, Jenny Humphrey was really the only character pushing against the status quo in terms of conscious fashion choices — her rebellious nature made her an edgy, punk antithesis to the rest of the characters at school. Blair had the UES prep school girl on lock, between her uniform look, her Hamptons wardrobe, and party attire. Serena had an easygoing, carefree air to her relationship with tradition, and her style reflected that. 

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