50. Lenny Kravitz
Band: Lenny Kravitz
All hail the king of the nose ring and aviator sunglasses. Kravitz's style has always straddled that line between bohemian and badass, and while not all of his style choices are necessarily praised-take for example the abnormally large scarf he was recently seen rocking-his wild outfit choices can't be denied. He also gets points for versatility, he knows how to tone it down while maintaining an attitude, thanks to an array of leather jackets and well-fitting basics like T-shirts and henleys.