February 22, 2009 - Jason Merritt/Getty Images North America more pics like this »
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61. Penelope Cruz, 2009

Penelope Cruz said she first saw this vintage dress by Pierre Balmain in 2001, but did not wear it until the 2009 Oscars. Lucky choice: not only did she nab the Best Supporting Actress Award, she did so while looking heartstoppingly romantic.