In the early 1930's, a boating enthusiast named Paul Sperry was walking his dog and became enthralled with how the pup handled himself while running on the ice. While inspecting the dog's paws, he discovered a natural herringbone pattern, the inspiration for the sole of what would become his signature, non-slip boating shoe, The Sperry Top-Sider. A perennial favorite for decades, in recent years, Top-Siders have grown in popularity thanks to a widening array of leathers, colors and styles. Whether you have plans to step foot on a boat or not, these classic loafers are a must have staple. If they're good enough for the U.S. Navy, they're good enough for me.