Shoes by Sperry, Classic design, A wardrobe staple, Slip-on style, Apron toe, Textured tread. Since 1935, Sperry Top-Siders have been the blueprint for the original boat shoe. Founded by avid sailor Paul Sperry, the prototype, and now signature non-slip traction soles were created after watching his Cocker Spaniel run across a frozen winter lake with incredible stability. Sperry's classic deck shoes and chukka boots now retain their iconic design but with contemporary finishes and colour ways.