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49. Rihanna in Dolce & Gabbana
In a sea of ball gowns, Rihanna made her mark at the 2009 Met Costume Institute Gala in a fierce satin tuxedo by Dolce & Gabbana. The menswear inspired ensemble had puffed sleeves, a white ruffle shirt, and a black bow tie. RiRi took her daring look a step further with a pair of black leather gloves and bold turquoise eye makeup.