13. Vans Half Cab (1992)
You know a design is a classic when everyone tries to copy it. The Vans Half Cab is no different. These sparked dozens of copycat shoes, but none could top the original. In fact, it’s still regarded as the best skate shoe ever made and is preferred by most professionals.
What’s great about these shoes is you could pull off wearing them even if you weren’t into skateboarding. The added bonus is they’d be so comfortable you wouldn’t even care that skaters would be making fun of you for being a poser.