(Celebrity)
Leighton Meester’s Hairstyle History Goes Way Beyond Her Iconic Headband
From slick bobs to baby braids.
It’s understandable of you still think of Leighton Meester in her Blair Waldorf best. That is to say decked out in preppy pieces accessorized with pearl jewelry and Chanel bags, plus her brunette hair pushed back with some type of headband or another. And while the Gossip Girl star’s iconic hairstyle has solidified its status in the pop culture zeitgeist, her 20-year career has included so many other well-coiffed moments worthy of mentioning — from the baby braids she wore as a teen to her current copper hair, which she debuted at Paris Fashion Week.
Like the most successful actors in Hollywood, Meester got her start with a cameo on Law & Order. Since that gig back in 1999 at just 13 years old, she’s popped up in dozens of films and TV shows. As her list acting credits grew, so did her repertoire of hairstyles. Of course some of these changes in style, length, and color were necessary for the characters she’s portrayed over the years, it’s clear that the Good Cop/Bad Cop star loves to mix it up in her real life, too. She’s unafraid to try more polarizing looks like baby bangs, but she embraces classics like Old Hollywood waves as well. But no matter what type of style she tries out, she always manages to make it look so effortless.
That said, if you’re in the market for some new hair inspiration, it might be time to take a look back into Meester’s hair history. With both casual and red carpet-worthy looks alike, her oeuvre is pretty impressive to behold — and you’re guaranteed to covet more than one.
Blonde Baby Braids, 2003
As a teen star in the Y2K, it was a right of passage for Meester to hit a red carpet in bedazzled tops and baby braids, like she did for the DVD debut of The Lion King in 2003. And wouldn’t you know it, the style is back in full effect today.
Bun & Bump-It, 2006
Another early aughts staples was the BumpIt, a tool that gave any hairstyle a boost of volume. Who knows whether or not Meester used the device for her mini pompadour and bun back in 2006, but regardless of how she achieved it, she managed to create a look that still feels relevant decades later.
Blair Waldorf Headband, 2007
What would a list of Meester’s best hairstyles be without including Blair Waldorf’s headbands? The mid-aughts look is still highly referenced (and repeated!) today.
Blonde Highlights & Beach Waves, 2008
Despite her close association with New York City (looking at you, Gossip Girl fans) Meester had a quintessential California girl moment in 2008 when she wore her highlighted lob in beachy waves for a shopping event.
Faux Bob, 2010
Proof that the The Roommates star loves trying out a bold beauty moment, she tucked her hair into a faux bob for a Harry Winston event in 2010. To make it even more daring, she paired the style with vampy, violet-hued lipstick.
Pretty Ponytail, 2011
The multiple time Met Gala attendee chose an extra long, extra sleek ponytail for the 2011 event. Dressed in a black LBD by Louis Vuitton, the perky pony gave her head-to-toe look a fresh, youthful feel.
Pushed-Back Bob, 2012
Meester went for a chin-length chop in 2012, and she wore her fresh bob a multitude of ways. One of the best was this pushed-back style that she paired with bright red lipstick.
Old Hollywood Waves, 2014
Despite its retro roots, Old Hollywood soft waves are a truly timeless hairstyle. But when Meester paired the look with a white cap-sleeved column dress by Antonio Berardi to the 2014 Tony Awards, it felt totally modern.
Platinum Blonde, 2018
The natural blonde bumped up the shade she was born with by a few notches back in 2018 when she debuted platinum hair with contrasting roots at the ABC/Freeform upfronts.
Micro Bangs, 2023
Meester snipped a set of baby bangs in 2023 and she’s been rocking some type of fringe ever since. For the Shazam! Fury of the Gods premiere, she balanced the severe style with long, soft waves which made the bangs feel so much more wearable.
Tousled Twist, 2024
The River Wild star loves a good updo moment, too. A memorable recent example is the artfully tousled twist she donned for the 2024 SAG Awards. With wispy bangs and tendrils, the hairstyle was effortless but still pulled together enough for a formal affair.
Copper Mid-Length Cut, 2025
This year Meester took lightened and warmed her brunette hue up a few notches. Celebrity colorist Amy Huson gave the actor her strawberry copper color, which was on full display at the Elie Saab Fall/Winter 2025 runway show in Paris.
