2. Lazaro Hernandez
Hustle: Fashion Designer, Proenza Schouler
As legend would have it, this half of the Proenza Schouler team had a fortuitous encounter with Anna Wintour on a plane (not that kind of fortuitous encounter) that indirectly kickstarted his career in fashion. Sure, we'd be nervous if we were pouring our heart out to the editor of Vogue on a cocktail napkin, but we'd also imagine that our classic casual look would make her think we were destined to be a star. Maybe Anna did notice that Lazaro has a way of making jeans and a tee look classy, all things considered — a phone call that got Lazaro a job at Michael Kors came soon after.