Sperry Top-Sider Authentic Original

Sperry Top-Sider's boat shoes are tried and true.

Despite expanding its brand to include sneakers, boots, flip-flops and other types of water-resistant footwear, Sperry Top-Sider's most popular model is the Authentic Original School Spirit 2-Eye boat shoe ($90). Similar to the first model that debuted in 1935, it pairs sure-footed grip with timeless style. If the white-on-gray color scheme isn't bright enough for you, try adding the free colored laces.