Rihanna in Giambattista Valli
Why We Picked Her: There’s just no one quite like Rihanna, 29. This risk-taker consistently wins at the fashion game by playing by her own set of rules.
What She's Said About Her Style: “I wanted to wear something that looked like it was floating on me,” she told Vanity Fair of her biggest fashion risk ever, the sheer Adam Selman gown she wore at the 2015 CFDA Awards. “But after that, I thought, O.K., we can’t do this again for a while. No nipples, no sexy shit, or it’s going to be like a gimmick. That night was like a last hurrah; I decided to take a little break from that and wear clothes."