Leighton Meester’s Style Evolution Through the Years

Meester attended the premiere of Holes in a silk bomber jacket, graphic tee, and cropped olive green pants. The outfit was the embodiment of the early 2000s style.

The young star wore a purple cami, flared corduroy pants, and a mustard yellow scarf tied around her waist for the Whipped Couture launch party.

The actress whipped out the cropped pants again when she arrived at an event wearing a ruched top, silver wedges, and ankle-length jeans. A sequined clutch and collarbone-grazing earrings provided the perfect touches.

Meester decided to go formal when she appeared on the Hot Hollywood red carpet in a strapless sea-blue dress with heeled black sandals.

She kept it casual when she attended the Man of the Year premiere in black cigarette pants, a red halter-neck top, and pointed heels. Her slouchy black knit bag is still on-trend today.

Meester was a vision in white when she attended a Motorola event in a sheer dress with sequined ballet flats.

The starlet donned a polished look at The Sopranos final season world premiere. Her pulled-back hair and open-toed heels matched effortlessly with her simple black dress.

What a blast from the past. Meester posed with her Gossip Girl co-star, Blake Lively, at the CW UpFront after-party. Meester is pictured in a flowy empire waist mini dress, while Lively opted for a ruched dress in a metallic green shade.

The two joined forces again while on the red carpet for the CW TCA party. This time, Meester stunned in a beaded and belted green dress, and Lively sported a vibrant yellow gown.

Meester kept the minidress theme going when she walked the Gossip Girl premiere red carpet in a sequined black and silver frock.

Who doesn’t love a night out at the ballet? Meester looked so elegant when she stopped by the New York City Ballet opening night gala in a head-turning black gown accessorized with a beaded clutch.

In 2007, Meester and Lively wore outfits that perfectly complemented each other. Lively was in an all-black ensemble with puffed shoulders and a beaded neckline, while Meester glowed in a ruffled gold dress with black heels.

Meester shook things up when she paired a leopard print babydoll dress with a pair of satin red pumps.

The Gossip Girl star was photographed wearing a glamorous knee-length caftan with shiny gold heels at a fundraiser fete. This ensemble looks like it was straight from the Gossip Girl set.

It’s easy to see that Meester is a fan of minidresses and mustard yellow. This fun dress she wore to the opera featured intricate waist detailing and a notched neckline.

This look screams Blair Waldorf. The actress wore a white dress with a sweetheart neckline for a Piaget event at Rockefeller Center.

How sweet was this belted, Jason Wu-designed chiffon look she chose for a CFDA cocktail party?

Meester served a blush pink look while stopping by the opening of the Chloe Los Angeles boutique.

Of course, Meester attended the Met Gala in a beyond-stylish look. For the 2009 event, she opted for a two-piece printed outfit designed by Louis Vuitton.

For a 2009 film screening in East Hampton, New York, she opted for an orange cloud-printed dress with cutouts at the waist and shoulders.