20. Canvas Shoes

Call 'em plimsolls or call 'em tennis shoes, but the O.G. sneaker came back around for a reason. The perfect subtle complement for summer—whether with shorts, jeans, or khakis—trickled down from Vans and up from Chucks, and met somewhere in the very comfortable middle.

LEADERS OF THE PACK:
Aprix, Vans, DVS, Supreme, Keds