From: Lexington, Mass.
Founded: 1935 

If you live in New England, there's a strong chance that you spent most of your life by the water. A boat shoe is imperative not only to wear to any sort of get together, but as an affirmation that you're from this part of the country. And there might not be a more iconic boat shoe brand than Sperry Top-Sider. Founded in 1935, the sea-experienced brand originally formed its deck sole concept from the New England winter; creating a shoe bottom that mimicked a dog's traction on an icy surface. The shoe would become so popular that the U.S. Navy would make a similar model for its sailors. It's been over 80 years and Sperry has become synonymous with summer, the ocean, and all things prep.