Year: 1989
Sneaker: Airwalk Prototype

As of the late '80s, the idea of a skate shoe was simple-high or low, with a vulcanized sole for board feel. Basically, Vans. In 1986 a guy named Bill Mann-or, more accurately, his 11-year-old son Mac-thought there was a lot of room for improvement. The company Mann founded, Airwalk, started with basic Chuck Taylor clones in wild colors, but in 1989 introduced the Prototype, an armored cupsole hightop that became the first "modern" skate shoe. Took long enough.