Leighton Meester’s Best Gossip Girl Outfits Of All-Time: Photos Of Blair Waldorf’s Chicest Looks

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September 7, 2023 11:50AM EDT

There is no denying Leighton Meester and Blair Waldorf are style icons. Take a look at the character’s best ‘Gossip Girl’ outfits here.

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Leighton Meester’s Best Blair Waldorf Looks

Leighton Meester’s Best Blair Waldorf Looks — There is no denying that Leighten Meister and her ‘Gossip Girl’ character Blair Waldorf are true fashion icons. The actress rocketed to fame for playing the prim and proper prep school diva on the teen soap opera from 2007 to 2002. Blair never let the show’s drama get in the way of her looking good. From break-ups to bad nights, and other scandals galore, the star never stopped being true style goals.

Blair loved girly silhouettes, often opting for ruffles, puff sleeves, and glamourous boys. Accessorizing was always big for the brunette beauty, who had a closet full of the perfect shoes, purses, and jewelry to kick a look up a notch. And she lives by the rule that there is no such thing as being over-dressed, always making sure her outfit is perfect for the occasion.

Want to take a look at some of Blair Waldorf’s best looks? Click through some gallery for some fashion inspiration from the Upper East Side.

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Leighton Meester On Set

Leighton Meester On Set — Leighton Meester looks amazing while on set of ‘Gossip Girl’ on Oct. 15, 2012. It looked like quite the fancy affair.

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Leighton Meester In Pink

Leighton Meester In Pink — Leighton Meester is pretty in pink while filming ‘Gossip Girl’ on Feb. 6, 2012. She had on a white jacket and a tiara as well.

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Leighton Meester In Floral

Leighton Meester In Floral — Leighton Meester is prim and promper in a cute dress and fuchsia heels while filming on Aug. 28, 2012. It was a great look for a city girl.

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Leighton Meester In Polka Dots

Leighton Meester In Polka Dots — Pretty in polka dots! Leighton Meester appears in the ‘Gossip Girl’ episode ‘Double Identity’ in 2010.

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Leighton Meester In Giambattista Valli

Leighton Meester In Giambattista Valli — Leighton Meester wears Giambattista Valli to film a scene with co-star Ed Westwick on Sep. 3, 2010. She carried a red folio under her arm and he looked rather dapper.

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Ed Westwick & Leighton Meester

Ed Westwick & Leighton Meester — Ed Westwick and Leighton Meester were quite the power couple on ‘Gossip Girl’. Here, they appear in the episode ‘Desperately Seeking Serena’ in 2008.

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Leighton Meester In Uniform

Leighton Meester In Uniform — As a student at Constance Billard prep school, Blair had to fid out how to style up her uniform. She wore a chic argyle water and two-toned heels for this 2008 episode.

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Leighton Meester & Blake Lively

Leighton Meester & Blake Lively — Leighton Meester and Blake Lively are bright in yellow during a scene from the 2010 episode ‘Goodbye Columbia’. Blake’s character Serena had a much more laid back style than her best friend.

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Leighton Meester In A Ballgown

Leighton Meester In A Ballgown — Leighton Meester looks anxious while wearing a white floral ballgown in the 2011 episode ‘Yes, Then Zero’. Her hair was styled to the side chicly and she carried a colorful clutch.

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Leighton Meester & Blake Lively Do Paris

Leighton Meester & Blake Lively Do Paris — Travel chic! Leighton Meester and Blake Lively are Paris girls in the 2010 episode Belles de Jour’

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Leighton Meester Sparkles

Leighton Meester Sparkles — Leighton Meester is totally dazzling in the episode ‘The Undergraduates’ from 2010. She made an entrance in her sequined dress.

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Leighton Meester At The Museum

Leighton Meester At The Museum — Work of art! Leighton Meester looks like a work of art herself while donning a ruffly, watercolor style dress to the Musée d’Orsay in Paris. The masterpiece Le Déjeuner sur l’herbe by Edward Manet was in the background.

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Leighton Meester In A Slip Dress

Leighton Meester In A Slip Dress — Heating things up! Leighton Meester goes for the lingerie-insppired look while wearing a red slip dress with black lace trim in the 2010 episode ‘The Witches of Bushwick’.

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Leighton Meester & Blake Lively In Soho

Leighton Meester & Blake Lively In Soho — Leighton Meester is so stylish in a collared Burberry number while filming with Blake Lively in the Soho neighborhood of NYC on Jul. 9, 2009 Blake wore a Rag and Bone dress.

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Leighten Meester Means Business

Leighten Meester Means Business — Leighton Meester is on the go in the 2009 episode ‘Gone With the Will’. She was on a mission in her classic black and white look.

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Leighton Meester In Teal

Leighton Meester In Teal — Leighton Meester is in full designer duds during an Oct. 13, 2008 episode of ‘Gossip Girl’. Her bucket hat was by Coach and she donned a zig-zag patterned Anna Sui top with a L.A.M.B. skirt.

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Leighton Meester In A Bubble Dress

Leighton Meester In A Bubble Dress — Leighton Meester rocks a pretty, pink floral bubble dress in the episode ‘Much I Ado About Nothing’. She had a beautiful flower in her hair and silk heels to match

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Leighton Meester Goes Glam

Leighton Meester Goes Glam — Leighton Meester goes for the full white-tie treatment in the episode ‘Hi, Society’ from 2007. She teamed her bowed, white dress with little gloves and a corsage.

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Leighton Meester In Red

Leighton Meester In Red — Leighton Meester is radiant in red in ‘I Am Number Nine’, a 2011 episode. Her hair was braided into a chic crown.

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