41. John Mayer
Band: John Mayer
John Mayer is a dude who has only recently found his style. His sartorial evolution, like his musical career, went through a very awkward phase. At first thrust into the spotlight for his radio-friendly songs and heartfelt lyrics, he adjusted to his newfound fame with a couple of tattoos and an affinity for expensive watches. As time went on, celeb relationships came and went, until his most recent, pensive cowboy phase. Introduced to visvim by Eric Clapton, Mayer began to fashion himself after the rock icons of yore, growing his hair out and wearing head-to-toe 'fits from obscure Japanese labels, looking like a modern outlaw rather than a bestselling singer/songwriter. It's this current version of himself that we hope he's remembered by, as a man who, after years of trial and error, seems to finally have found his style.