Ever since Paul Sperry created the first pair of top-siders in 1935, boat shoes have become a classic style staple. Their preppy, iconic look goes well with almost any summer look, whether you’re on a sailboat in New England or not. Because of their simple design, they will look as good with a pair of shorts and a polo as they would a swimsuit or khakis and an oxford cloth button down. Nowadays you can get your Sperry Top-Sider in any color imaginable so you can be understated or bold. Even better, if you get a classic leather pair for this summer, not only will they still be in style next summer but they will also have that perfectly broken in look that makes them even cooler.
(Above Sperry Top-Sider boat shoes – $95 from Nordstrom)