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6 Lupita Nyong'o's Prada Oscars dress, 2014 Kevin Winter Images Lupita Nyong'o landed her breakthrough role in 12 Years A Slave straight out of Yale, and marked a string of firsts when winning an Academy Award for Best Supporting Actress (the first African or Mexican actress to win the award and the first Kenyan actress to win an Oscar)

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SHOP THE LOOK: JUPITER BLACK MAXI DRESS

10 Trucker Hats Steve Granitz Images In the early 2000s, lots of celebs made their red carpet looks more casual with a trucker hat