16. Steve Jobs — New Balance 574

When: Early '90s

Where: Photoshoot

So hey, what do you think these guys were talking about? You have to admire the computer geeks for their consistency. Bill Gates still rides the nerd look hard, although he's since graduated to somewhat cooler glasses, and Steve Jobs stayed in grey New Balance until his untimely death in 2011. Glad he abandoned that haircut, though.