Once in a while, a show comes along that leaves such a strong, indelible imprint on fashion and culture that its legacy continues to be felt long after it ends. Sex and the City is the most notable example. So is Gossip Girl. What Carrie Bradshaw did, sartorially, for ambitious 30-something women was mirrored by the rich, catty, impeccably-dressed coeds of Constance Billard for fashion-obsessed teens of the early aughts. And no offense to the recent HBO Max reboot of Gossip Girl, which has introduced the Gen Z set to a new class of style stars, but Blair Waldorf, Serena van der Woodsen, and their ilk will forever remain the OG fashion icons of the GG ecosystem.
Blair's eclectic, preppy polish, Serena's je ne sais quoi boho chic, Chuck's impeccable tailoring—they are all still very ripe for wardrobe inspiration. And so what if no kid on the Upper East Side actually dresses like this? That is what Halloween is for. Whether you're in need of ideas for a closet refresh, or just want to be the chicest person come October 31st, below are the best outfits to recreate from the original Gossip Girl.
Dynamic Duo: Blair Waldorf & Serena van der Woodsen
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Blair and Serena's friendship status may have changed often throughout Gossip Girl's six season run, but each character's singular sense of style was thoroughly consistent—even when layered over a school uniform. For a Blair-worthy Halloween costume, stock up on such essentials as prim pumps, pretty blouses, and sleek, colorful outerwear. For Serena-inspired dressing, master the uptown/downtown balance with slouchy boots and a buttery leather jacket worn with a preppy plaid skirt.
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Queen B: Blair Waldorf
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Romantic and feminine touches with a hint of cinematic nostalgia—a chic hat, structured bag, bows, silk, a flowy silhouette—are obligatory for any style homage to Blair. So is a robust arsenal of tights.
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Perennial It Girl: Serena van der Woodsen
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This look perfectly sums up Serena's worldly cool. The breezy wide-legged pants, turquoise necklace, and fedora (not to mention the giant Fendi) are effortless indicators of a jetsetting lifestyle, while the loafers add a bit of that signature van der Woodsen quirk.
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Dapper BFFs: Nate Archibald & Chuck Bass
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Chuck's knack for eccentric color combinations and Nate's brooding rich-kid-off-duty style are two Halloween costume ideas that are easy to replicate. For Chuck, go for clean chinos in a bright hue, plus other UES staples like a button-down, cardigan, and classic trench. For Nate, incorporate sporty accessories—bonus points if you can pull off his tousled hair, too.
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Little J vs... Little J
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Ever the enterprising social climber, Jenny Humphrey went through quite the style transformation on Gossip Girl, from her eager Blair-wannabe early years to her brief reign of terror as Constance Billard's bad girl queen bee. Either way, you can't really go wrong with whichever iteration of Little J you choose for Halloween this year.
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Brooklyn Import: Dan Humphrey
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Dan Humphrey fully embodied the Brooklyn hipster stereotype and it's an aesthetic that can be turned into a simple Halloween costume with just a few quintessential separates—a plaid shirt, Chelsea boots, a New York coffee cup, and a distressed messenger bag.
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9 Halloween Costume Ideas Inspired by the Original 'Gossip Girl' - How to Recreate Gossip Girl Outfits - TownandCountrymag.com
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