Bottom line, the boat shoe is the sneaker of the seas; a casual, daytime-skewing piece of footwear best enjoyed without socks or Slack alerts. None of this is written in stone anywhere (that we know of), and you retain your legal right to freak anything, anytime. But if you’re in doubt about the boat shoe’s sea-worthiness at an establishment or event, we’d suggest going with something even slightly more formal to avoid any “uncle who only wears Hawaiian shirts” energy. What to Wear With Boat Shoes As per our previous section, you can pull off boat shoes with most of your closet. Shorts or a bathing suit are absolute no-brainers. (Nothing goes from beach to boardwalk like boat shoes.) As are jeans — maybe in white or off-white, because it’s summer, and why not — as well as trousers, linen pants, and every type of chino under the sun, wide-legged or straight, pleated or flat, beige or covered in small embroidered whales. Up top, if you can wear it with jeans or chinos, it’ll go great …