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Meester at the Metropolitan Opera in 2008 in a sunny, strapless Yves Saint Laurent dress. This gorgeous look needs nothing else...but that bold red lip is utter perfection.
That same year, she wore a white strapless Nina Ricci dress to a Piaget party, providing a pristine backdrop for her diamonds.
Meester goes ladylike in Jason Wu at the CFDA/Vogue Fashion Fund party in 2008. The asymmetrical hem and red belt make this a slightly artier version of something Blair Waldorf might have worn.
For a front-row appearance at a Proenza Schouler show in 2009, she was ready for the tent’s many paparazzi in a copper sequined top and jewel-toned emerald skirt.
The actress got a lot of comments—pro and con—for this Louis Vuitton ensemble at the Costume Institute Gala that same year. We applaud a fashion risk and this one upped her fashion cred substantially.
Meester goes graphic in an oversized houndstooth print Emilio de la Morena shift dress at the screening for 500 Days of Summer. Note the simple hair and accessories—a key part of sporting such a bold look.
With a few seasons as Blair Waldorf under her belt, Meester’s style confidence really began to emerge; in this ethereal Tomas Maier for Bottega Veneta dress, she was a red carpet star at the 2009 Emmys.
At Phillip Lim’s spring 2010, she wore an adorable nude frock with a belted cardigan. The grey booties give the otherwise cozy look some needed edge.
Look closely: you don’t want to miss the delicious suede bag Meester wore to the Proenza show in 2009. It’s the most sumptuous eggplant color.
Meester wears classic Prabal Gurung to a New York Public Library benefit in 2009. The signature bow is subdued by the light colors of the dress and simple accessories.
Versus got an injection of cool when designer Christopher Kane took the reigns in 2009. Meester paired his blue satin bandage style dress with Christian Louboutin shoe booties to the Fashion’s Night Out 2010 runway show.
Electric blue pants become almost subtle when paired with a simple black top and accessories at a screening party for The Romantics in 2010.
A little black dress by Chanel was the obvious choice for the Soho boutique’s re-opening in 2010, but the statement necklace and cat’s-eye makeup take this look up a few notches.
Another bold choice in Meester’s evolving style: this black and white Prabal Gurung dress at the 2010 CFDA/Vogue Fashion Fund Awards. We like a shot of color (A red lip? A cobalt clutch?) with such a stark color palette, but she can’t bat a thousand every time.
Our favorite look of the actress-slash-songstress (remember "Good Girls Go Bad"?). It takes some chutzpah to wear a plunging, sheer lace jumpsuit, and she does it with aplomb in Marchesa at a Harry Winston benefit event in 2010. Britneys and Lindsays of the world, take note—this is how it’s done.
At a time when most young starlets go for barely covered mini-dresses or down-to-there slashed gowns, Meester’s pale water-color, long-sleeved gown from Burberry Prorsum (with Jimmy Choo heels, Louis Vuitton clutch and Cathy Waterman jewelry) at the 2010 Golden Globes was radically elegant.
The newly-appointed spokesperson for the Vera Wang fragrance Lovestruck goes classic in a copper-colored silk ruched dress from the designer at a charity event earlier this year.
When we saw Louis Vuitton’s fall 2011 collection, we dubbed it as S&M chic. We never imagined we’d see it on the red carpet, but Meester has done it, and well. The rigorous lack of accessories and swept-back ‘do keeps the look demure—perfect look for this year’s Met Ball.