Why she wins: Like Rita Ora, Rihanna is an undeniable risk-taker when it comes to fashion. She isn't afraid to mix the funkiest of pieces, on stage or on the streets. In Rihanna's world, the bolder the better. The singer did a little peekaboo action with a sheer white blouse, white shorts, and other crisp white add-ons in London.
Her Summer staples: Crop tops, ankle-strap sandals, denim, statement sunglasses.