8 Blair Waldorf Outfits to Recreate for the Perfect Upper East Side Fall

Allow Queen B's timeless ensembles to inspire you this season.

blair waldorf outfits

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Even while staying Switzerland-neutral on the quality of Gossip Girl’s recent reboot, it’s safe to say there will never be an Upper East Sider with as much style as the original Blair Waldorf. Perhaps it was the era of peplum and headbands that paved the way for some unforgettable looks, or maybe some things are best summarized in that famous moment during season two when Serena says, “Not everyone wants to be Blair Waldorf.” Without missing a beat, Blair responds, “Not everyone can be.”

I phoned "Part-time Gossip Girl historian and Full-time Editor-in-Chief of Fashionista," Tyler McCall, for help on deciphering just what makes some of Blair’s greatest hits so Blair. Her insight plus this fall’s new pieces create a style guide to autumn in New York fit for uptown royalty. After all, according to Queen B, “Fashion is the most powerful art there is….It shows the world who we are and who we’d like to be.” Below, eight of Blair Waldorf's most memorable fashion moments, and how to recreate them for the ultimate Upper East Side fall.

Wedding Day Blues

"This Elie Saab couture look is unquestionably Blair's best wedding look," McCall points out. With a much more traditional wedding look in the books, this dress celebrated what made her relationship with Chuck so...unique? Try out a shimmery blue for a formal event this fall. Take notes from Blair by piling on the glamour with a silver headband silver shoes.

White After Labor Day

According to our resident expert, "There is no question this white Marc by Marc Jacobs dress is one of Blair's most all-time iconic looks; If you try and find this on resale sites, you're going to pay an arm and a leg." It's not the dress that makes the woman, in this case. McCall continues, "I think that's probably because she wears it in the iconic "three words, eight letters" scene with Chuck." Whether you're romanced by the idea of an all white look post-Labor Day or not, there's something chic about the monochromatic outfit. Throw a white sweater over your shoulders and you're ready for wherever a pool party in the Hamptons might take you.

Back-to-School Chic

Perhaps the most iconic of the sartorial categories Blair finds herself tackling is the private school uniform. "This was the first time we saw Blair in uniform, so it really sets the tone for what we can expect from her and how she contrasts with Serena: Headband locking every strand in place, prim details, and preppy silhouettes," says McCall. The high neckline plus the plaid skirt feels very of the moment. The white tights? Maybe next season.

Inspired by the '60s

According to Tyler, this is "another iconic Blair look," thanks to the details. "Peep the matching pearl bracelets—an Uptown take on double-cuffing," she explains. "This outfit really exemplifies for me how Blair dresses very intentionally; Everything feels carefully considered, like the way the pattern in the tights mirrors the lace on the dress." Let the drama of the bell sleeves speak for themselves in this more pared-back take on the look. But keep the drama of the pearls. It's Blair Waldorf-inspired, after all.

Florals for Fall


Welcome to Paris! And welcome to season six, one that was famously low on strong outfits. "I don't really think of Blair as being a Dolce & Gabbana girl, but this is a fun take on what she'd wear galavanting around Paris," McCall says. While the original runway look is certainly more interesting, kudos to Blair for shaking things up with a matching set. "On anyone else, a beret would look kind of trite, but there aren't many hair accessories Blair can't make work," continues McCall. The below outfit pays tribute to the look, featuring a dress that feels like a skirt set and a hat worthy of a queen.

Purely Pastels

"We so rarely ever saw the cast during warm weather. Typically, the show occurred very late summer through early spring, so I always get a kick out of seeing Blair in fewer layers," explains McCall when describing this "underrated Blair look." It's undeniable that even in a skirt and a sleeveless blouse, Blair appears collected. Baby blue is having a big moment. Try embracing the hue in a flirty skirt. And in the essence of Miss Waldorf, add a massive bow in the place of two tinier ones.

High Neck, High Society

This look is perfect for fall. First, consider the transitional dress. "The ruffled collar adds an aristocratic edge to an otherwise standard floral dress," notes McCall. Second, just one of Blair's enviable coats. In a moment of uncharacterized outfit repeating, Blair Waldorf proves subdued tones are just as chic. In the words of a true New Yorker, McCall envies Blair's coat collection, adding, "now that I live in the city, I wonder how she has the space." Modernize the look by adding some tall suede boots.

Blair and the Bandage Dress

Certainly an unexpected combination, but Blair does hate to be boxed in, style-wise. McCall breaks down the mid-crisis dress by explaining that she's "been rejected from Yale for bullying her teacher and Chuck won't commit, so she drops the good girl veneer for a bit." Take notes and next time you're feeling the pressure, slip into something like this Staud dress. But stay true to your style, just like Blair. "I don't remember ever seeing the Kardashians jazz up their Hervé Leger dresses with cardigans and pearls," reminds McCall.

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