AfterPay Available - Exuding nautical style since 1935, this is Sperry's iconic Authentic Original. Credited as the very first boat shoe, the often-imitated silhouette is built on a moccasin-stitched leather upper featuring a 360-degree lace wrap system for a secure fit. However, the A/O's most distinct feature lies beneath: the subtle wavy siping cut into the rubber outsole, improving traction on wet and slippery surfaces. While still relevant as a shoe for the sea, Sperry finds a new audience in the sartorial crowd with its timeless, preppy aesthetic.