Prep Essentials: Sperry Top-Sider

One of my pairs of Sperry's at the beach

Every prep loves boat shoes. Naturally, this comes from the prep's love of boats. Sperry Top-Sider is the original brand, and still the favorite among preps. Paul Sperry first invented the boat shoe in 1935. His motivation came from his cocker spaniel, Prince. Sperry noticed that the dog kept its traction on the wet boat because of all the cracks going in different directions on the bottom of Prince's paws. This design became known as Razor-Siping and are still used on the soles of Sperry's today.

These shoes are some of the most comfortable shoes available on the market. Sure, at first you may get blisters trying to break in a new pair, but those rough first couple of days are well worth the results after. The best way to break in a new pair of Sperry's, besides wearing them a lot, is to get them wet. The water will soften the leather and help them to better conform to your foot. Just remember, wearing a pair of Sperry's with socks is like wearing a pair of sandals with socks; you just don't do it. There is one exception to the no socks and Sperry's rule, though: if you are wearing your Sperry's with pants, it is acceptable to wear dress socks with them.

While many preps still prefer the authentic original shoe, Sperry has hundreds of different colors and styles so matter what your style is, you're sure to find a pair of Sperry Top-Siders that you'll love. Depending on the style, Sperry's can be worn for super casual events all the way up to semi-formal events. The classic brown leather Authentic Original boat shoes go great with a pair of chinos and another prep essential, the blazer.

Sperry is also a strong advocate for ocean and wildlife preservation so it's a great company to support. Check them out online.