Year: 1989
Sneaker: Vans Caballero

Vans lost their way a little bit in the mid-'80s as skaters who grew up in Authentics and Eras and styles 36 and 38 moved on to inexpensive basketball hightops. They offered more protection, and best of all they were cheap-a must when a pair of sneakers lasted two weeks at best. In 1988, though, Vans was prepared to make a comeback. They signed pro skater Steve Caballero, and the following year gave him a signature hightop of his own, the Caballero.