Colorways: Black/White
Year Released: 1992

If there is ever an actual sneaker hall of fame, the first person to cut down the Vans Caballero deserves to get in on the first ballot. Removing a majority of the ankle collar converted the bulky Caballero into a lean and mean skate shoe, reflecting the transition of skateboarding itself from vert to street. Twenty years after its initial introduction, the Half Cab is still considered the best skate shoe ever.