23. John Mayer

Complex says: Over the years in the few times John Mayer has been caught out in public he has always had something classic looking and fresh on his feet. From the Kennedy-inspired New Balances that made just about every "best of" list in 2011 to a plethora of Blazers, Dunks, Air Maxes, and other runners. There was even a blog dedicated to his footwear choices — not your usual fangirl stuff. And his love isn't superficial. In 2006, he told the AP "I'm actually into sneakers on a design level. I've got a big design thing going on in my life right now ... I love designing stuff. I mean, my biggest dream, forget Grammys, I want to be able to design an Air Max."