Leighton Meester achieved household name status in the late aughts with her role as Upper East Side teen Blair Waldorf in the hit CW series, Gossip Girl. Meester’s character, the frenemy of Blake Lively’s Serena van Der Woodsen, quickly became a style icon in her own right, wearing everything from Oscar de la Renta gowns to fresh off-the-runway Marc Jacobs looks until the show came to an end in 2012.
Like many actors with such recognizable on-screen personas, Meester’s personal style often blends into that of Waldorf’s—even all these years later. She favors simple, unfussy silhouettes with a bit of preppy chic sprinkled in, just as Waldorf would prefer. But that’s not to say Meester, who often pops up on the red carpet with her husband Adam Brody, doesn’t have fashion signatures of her own. She loves a tea-length floral look from Chanel or Marni, a simple white dress, and even something more daring like the gilded Emilio Pucci number she wore to the 2014 Met Gala. Here, look through Meester’s red carpet evolution from Gossip Girl until now.
2025: SAG Awards
Meester put an elegant spin on the naked dressing trend in her lace Elie Saab gown.
2025: Golden Globe Awards
Meester looked like a goddess in lime green Versace at the 2025 Golden Globes which she attended with her husband Adam Brody.
2024: SAG Awards
The actor, dressed in custom St. John, leaned into quiet luxury at the 2024 SAG Awards.
2023: Shazam! Fury of the Gods Los Angeles Premiere
Meetser, rocking ’70s fringe bangs, looked ready to party in this lamé dress with ruffles.
2022: Fleishman Is In Trouble Premiere
Simple tea dresses with floral details are a staple of Meester’s red carpet style.
2019: Shazam! Premiere
For a 2019 premiere, Meester went with a patterned Alessandra Rich look and black accessories.
2018: American Music Awards
Meester showed up to the 2018 AMAs in a cut-out Sonia Rykiel confection done in black and white.
2018: ABC Upfronts
Meester elevated her platinum blonde hair with this floral Marni dress.
2017: Golden Globes Party
The actor added a pop of blue to her white Galvan for a 2017 Golden Globes party.
2014: Tony Awards
Meester did her version of old Hollywood in a white Antonio Berardi dress paired with a red lip and tousled waves.
2014: Met Gala
The actor’s Emilio Pucci dress at the 2014 Met Gala was bejeweled to perfection.
2012: MTV Movie Awards
The actor proved that hot pants are red carpet-appropriate in 2012.
2012: Met Gala
Meester, dressed in a Marchesa ball gown, looked like royalty at the 2012 Met Gala.
2011: Met Gala
Messter is known for her feminine frocks, but this Louis Vuitton bandage dress she wore to the 2011 Met Gala tapped into her riskier side.
2011: Golden Globe Awards
The 2011 Golden Globes called for a ladylike Burberry dress slit up the center.
2009: Emmy Awards
The actor looked ethereal in Bottega Veneta at the 2009 Emmy Awards.
2009: Teen Choice Awards
Messter was ahead of the “pop of red” trend when she wore bright red pumps with her striped Louis Vuitton dress.
2008: CW Event
Meester picked out a patterned Chloé number to attend a 2008 CW event in New York.
2007: Gossip Girl Premiere
The actor accented her Julie Haus party dress with a short hair cut and strappy black heels.
2007: CW Summer Tour Party
Meester and her Gossip Girl co-star Blake Lively coordinated in bold jewel tones.
2006: Man of the Year Premiere
The actor elevated her red going-out top with black skinny jeans and heels.
2003: Whipped Couture Launch Party
Wearing a purple lace top and flare jeans, Meester showed off her aughts style in 2003.
2003: Holes Premiere
When capri pants were still in style, Meester paired hers with a baby pink tank top and multi-color bomber jacket for a 2003 premiere.
