Date: 1988

There was a dark time in skateboarding during the '80s. Vans had run into financial troubles and Airwalk/Etnies/et al didn't exist yet, so even the most well-known professional skateboarders were scrapping for footwear. So when a re-structured Vans signed Steve Caballero to a proper endorsement deal, this was big. Less than a year later they released the Caballero hightop, and a few years after that the prevalence of street skating led to some enterprising soul to cut down his Caballeros into what would become the "Half Cab."