Nerd Icon: Steve Jobs of Apple
Steve Jobs was famous for a lot of things, duh. Among them was his uniform of a black Issey Miyake mock neck, Levi's 501 dad jeans, and New Balance 992s. It wasn't the most stylish thing on the market, but it worked. Think about it: how many tumblr style icons are now wearing super washed jeans and New Balances? Was Jobs a fashion visionary? That's debatable, but what is true is that he knew what he liked, and thanks to the cyclical nature of trends, what he liked was sooner or later guaranteed to become the next big thing. Sometimes it's best to wear what you want and nothing else.