19. Kid Rock

With his lifetime supply of awful hats, dirty wife beaters, and the occasional pimptastic hoodie, Kid Rock's “American badass” schtick is giving American style a bad name. We'd much prefer the USA to be identified with, say, Bruce Springsteen's Levi's 501s and crisp white tees... and, if we want to paint a truly honest American picture, maybe a pack of Marlboros rolled up in the sleeve.