Even if you’ve never stepped foot on a boat before, there’s a strong possibility you’re familiar with boat shoes. You’re probably familiar with Sperry’s take on the shoe, but for those who aren’t, boat shoes are two-hole, leather shoes that are breathable and waterproof — and made with a rubberized sole that provides critical traction for slick surfaces like a boat deck. Inherently functional, boat shoes have found a second life a casual office shoe, a go-to choice for collegiate prepsters, and even get referenced by Jay Z himself.
The boat shoes of 2020 aren’t quite as boxy as they were in the past and are now more reflective of the sleek sailboats you’d typically wear them on. The key to pulling them off is to know that they shade a little more towards the casual side of the spectrum. That means you can wear them with jeans or khakis with ease. Regardless of how you style them, we’ve rounded up nine of our favorites that can take you from the shore to the water and back again.