#1. Vans Half Cab
Sorry to disappoint other shoe brands, but this is by far, hands down, the best skateboard shoe ever created for more than one reason. It's been in the Vans line for 20 years and is the longest running pro skateboard shoe in history. It's been knocked off to hell and back by a grip-load of other shoe brands and when it comes down to it, this shoe was ahead of its time with what skateboarders looked for in a true skateboard shoe.