‘Gossip Girl’ Stars Dressed Like Their Iconic Characters In Real Life: Photos

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May 19, 2022 12:58AM EDT

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‘Gossip Girl’ Stars Dressed Like Their Iconic Characters In Real Life

‘Gossip Girl’ Stars Dressed Like Their Iconic Characters In Real Life — Hey Upper East Siders! When Gossip Girl premiered on the CW in September 2007, one element of the show immediately resonated with fans: the fashion. Whether it was Blair’s preppy wardrobe, or Chuck’s seemingly endless number of suits, Gossip Girl devotees couldn’t get enough of the now-iconic early 2000s ‘fits! Although the characters, who we were first introduced to in the young adult novel series by Cecily von Ziegesar, seemed larger than life, there are times when life imitates art. Or I guess we should say, when Gossip Girl actors imitate their on-screen counterparts. As rumors continue to swirl about whether or not the cast will come together for a reunion, or better yet a reboot, we’re looking back at 11 of your favorite actors, and the times they dressed just like their characters.

From Blake Lively to Taylor Momsen, there were so many Gossip Girl actors whose on-screen style totally translated into street-style goals! Scroll through the gallery above to see more of your favorite stars rocking outfits similar to their Upper East Side characters.

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Blake Lively Dressed Like Serena Van Der Woodsen

Blake Lively Dressed Like Serena Van Der Woodsen — Blake looks like it-girl Serena in a black and white ensemble, and a wide-brim black hat. So chic!

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Leighton Meester Dressed Like Blair Waldorf

Leighton Meester Dressed Like Blair Waldorf — Although Leighton is much more dressed-down IRL when compared to Blair, she has been spotted wearing floral dresses and skirts that are reminiscent of her character.

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Chace Crawford Dressed Like Nate Archibald

Chace Crawford Dressed Like Nate Archibald — Much like his on-screen counterpart, Chace Crawford loves a suit! He looks so dapper here in a charcoal grey ‘fit, and looks just like Nate (minus the baby face).

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Penn Badgley Dressed Like Dan Humphrey

Penn Badgley Dressed Like Dan Humphrey — Penn Badgley AKA Dan Humphrey AKA Gossip Girl has come a long way since the show wrapped! He’s currently starring in psychological thriller series ‘You’, one of Netflix’s most binge-worthy shows, and while promoting the show he’s been rocking outfits that totally remind us of ‘Lonely Boy’ Dan.

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Taylor Momsen Dressed Like Jenny Humphrey

Taylor Momsen Dressed Like Jenny Humphrey — Taylor Momsen’s Jenny went through a dramatic makeover on-screen, and totally reflects the actor’s IRL style. It’s clear Taylor is a big fan of the rocker-chic aesthetic, much like Jenny in later seasons of the show.

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Ed Westwick Dressed Like Chuck Bass

Ed Westwick Dressed Like Chuck Bass — If there’s one thing that’s synonymous with Chuck Bass, it’s his suits. British actor Ed Westwick served major Chuck vibes in a dapper, navy blue suit jacket.

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Jessica Szohr Dressed Like Vanessa Abrams

Jessica Szohr Dressed Like Vanessa Abrams — Jessica Szohr definitley channelled her character Vanessa Abrams when opting for a relaxed, boho-style off-the-shoulder dress.

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Michelle Tratchenberg Dressed Like Georgina

Michelle Tratchenberg Dressed Like Georgina — Michelle Tratchenberg played Georgina Sparks, the character we all loved to hate, and she’s brought some of the character’s preppy chic style with her out into the real world!

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Kelly Rutherford Dressed Like Lily Bass

Kelly Rutherford Dressed Like Lily Bass — Kelly Rutherford ruled the Upper East Side as Lily Van Der Woodsen (or should we say Bass), and still pulls together outfits that remind us of her character!

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Elizabeth Hurley Dressed Like Diana Payne

Elizabeth Hurley Dressed Like Diana Payne — Elizabeth Hurley’s turn as Diana Payne saw the British bombshell serving looks in plenty of cocktail dresses. This red outfit totally reminds us of her days on Gossip Girl.

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Matthew Settle Dressed Like Rufus Humphrey

Matthew Settle Dressed Like Rufus Humphrey — Matthew Settle played Rufus Humphrey, the ultimate Brooklyn dad. He was often dressed down, but he could totally pull off a suit as well!

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