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Jason Wu

Modeled by actress Anna Kendrick

In the beginning: Once an intern at Narciso Rodriguez, 27-year-old Wu shot to stardom after making Michelle Obama's one-shouldered white gown for the inaugural balls. Known for: Frothy but unfussy evening wear, dresses, and suits. Tidbit: He also designs incredible doll clothes for Madame Alexander. The next... Oscar de la Renta. Famous fans: Reese Witherspoon, Kerry Washington, Natalie Portman.

Dress, $3,910.

Read our interview with Up in the Air's Anna Kendrick
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