Sanuk Scurvy Shoe - Boys' - $27.27

Sanuk stitched boat-style canvas uppers with classic sneaker soles to create the Boys' Scurvy Shoe, which is all your boy needs to scramble around the park (well, he contends that he needs a puppy too). Set him loose in these comfy, playfully-styled shoes and let him busy himself with a longboard, bike, or tree-climbing sesh. - $27.27