46. Duck Boots

These rainy-weather essentials got a style upgrade in the Aughts. The L.L. Bean joints were still classic, but more design-heavy versions became a cool-guy favorite. No matter the kind, these boots are perfect for jumping in puddles and fucking up other peoples' days. Splishy-splash!

LEADERS OF THE PACK:
L.L. Bean, Polo Ralph Lauren, Gourmet