Skater: Steve Caballero
Year: 1993

Forget the best signature skate shoe ever, the Vans Half Cab is probably the best skate shoe ever, period. The cut-down version of Steve Caballero's signature hightop emerged organically, as street skaters sought freer movement and broke out the X-Actos and duct tape. Twenty years later, the vulc mid-cut has no shortage of imitators and no shortage of praise.