Lenny Kravitz

Musician, 56

Skipping six buttons and tying your shirttails in a tight knot above your belt buckle shouldn’t look good on anyone. On Lenny Kravitz, it looks fantastic. Can we all pull off the kinds of looks he can? Nope! But we should absolutely channel the sort of confidence and creativity that lets him not just break the style rules but also render them entirely moot.