Dogtown and Z-Boys (2001)

Director: Stacy Peralta

Packed with footage from the 1970s and beyond, this documentary on skating's early days oozes with old-school style and enough Vans to fill an empty pool. It's hard to narrow down just one awesome look, but the combination of wild hair, small T-shirts, short shorts, and knee-high gym socks has definitely thrashed its way into skateboarding history.