33. Rivers Cuomo
Who cares about his sweater? Don't destroy his glasses. Cuomo's thick frames characterized the geek rock movement of the '90s, while his sweater vests and slim-fitting polo shirt set a precursor for sensitive skinny dudes who were somehow managing to get laid. He was the archetype for every other indie guy with a cute Japanese girlfriend, and his affable-looking sweater vests and non-threatening wardrobe choices essentially set the bar for how Fred Armisen's character dresses on Portlandia.