36. Boat Shoes

Sneakers felt like they'd already peaked (this was before grown-man sneakers came along, when everyone was drowning in bright-ass splashes like the greedy geniuses they were), and hard-bottom shoes felt a little stuffy. So, if you think about it, the rise of the boat shoe was pretty much inevitable. With a more sophisticated silhouette, and enough color/pattern variety to satisfy the most voracious of hypebeasts, the summertime yacht bonanza crossed over to the skreets and became a phenomenon.

LEADERS OF THE PACK:
Sperry Top-Sider, Sebago, Vans, Band of Outsiders for Sperry