The Sperry Top-Sider was inspired by a dog named Prince? Paul Sperry was intrigued by his cocker spaniel's ability to run nimbly over ice and snow. Upon turning Prince's paw over Sperry observed hundreds of tiny cracks and cuts in all directions. Sperry, in turn, was anxious to get back to his workshop to start his own experiments.
Grabbing a quarter inch thick piece of gum rubber he began cutting a herringbone shape into the material with his pen knife. The first pair of boat shoes were a worn out pair of sneakers with a quarter inch piece of herringbone patterned gum rubber glued to the bottom.
For more information on the involvement of Converse and Abercrombie & Fitch in the growth of the iconic boat shoe visit Sperry's site and download Paul Sperry's original story. It's a great read.