Madonna

Madonna: 50 Looks We Can't Forget

As the Material Girl celebrates a half-century, trace her every fashion reinvention. By Aaron Parsley and Cara Lynn Shultz

THAT GIRL

In the 1987 crime romp Who's That Girl, Madonna played a spunky but ditzy ex-con named Nikki wearing – what else? – a leather jacket, fingerless gloves and a miniskirt. "There was just something about the character – the contrasts in her nature, how she was tough on one side and vulnerable on the other – that I thought I could take and make my own," she told Rolling Stone.