The 20 Best Boat Shoes for Men, Tested by Style Experts

Cutting to the chase is the OG design that has never looked out of style and definitely never will. In fact, we believe that every man should try on this seaworthy style that has remained so popular for decades because they're just so comfy, you'll want to wear them all the time. The leather, for instance, is meticulously hand-sewn for enhanced durability and graceful aging. As you slip your feet into them, you'll also find yourself reveling in the secure, customized fit provided by the signature 360° lacing system. The tried-and-true outsole with razor-cut wave-sipping also offers unrivaled traction for true seafarers.

What we love most about these OGs is that they now come with an OrthoLite insole to envelop your underfoot in comfort and provide shock absorption to each step. Coupled with the inclusion of an EVA heel cup that adds an extra layer of cushioning, we were even able to travel in these shoes for hours.

A wise word, however: while we found Sperry's boat shoes effortlessly easy to break in, they do tend to stretch ever so slightly with each wear. Therefore, we warn against sizing up here for these.