It's the shoe that graces the cover of The Official Preppy Handbook so the Sperry Top-Sider's preppy bonafides are well established. But how did it get its distinctive name? The Top-Sider was ...

Shown are several new colorways in the latest offerings from storied deck shoe brand Sperry. Utilizing both canvas and suede, the shoes take on tonal uppers with contrast stitching and laces.

Image Boat shoes are rooted in function, not fashion. But to some, their anti-fashion vibe is part of their appeal.Credit...via Sperry The Top-Sider is “the Platonic ideal of the shoe,” said ...