Notable partners: Blake Lively, Toni Garrn, Erin Heatherton, Bar Refaeli, Gisele Bündchen 

Leonardo DiCaprio is a trip. He's usually one of the most stylish on the red carpet. But when he isn't on the job, and is just running errands or hanging out with Erin Heatherton, he looks like a regular Joe...which is kind of a dis to "Joe." Newspaper boy hats, cargo shorts, white socks with slip-ons, and the occasional mandal—a complete 360 from his sharp suits. 

Surprisingly, there are websites, forums, and even an eHow page on how to imitate DiCaprio's style—all dead ends, though, because you're already a lost cause if you're looking for style inspiration there.