Here's How to Wear Boat Shoes the Right Way

Sperry is one of the most popular brands of boat shoes in the U.S. SPERRY

When it comes to men's fashion, boat shoes are one of the most elusive trends. They're comfortable, casual and fashionable—if worn correctly, of course—but a lot of men (and even women) aren't sure how to wear boat shoes the "right way." Are you supposed to wear socks with boat shoes, or is that a total fashion faux pas—like when men wear socks with sandals? Should they be tight or loose? And can you only wear boat shoes on a boat?

How you style your boat shoes can make or break your look, whether you're wearing them on a yacht, to the office or on a date. Avoid committing an unforgivable style crime by learning how to wear boat shoes the right way with our four best tips.

What is the right way to wear boat shoes?

When it comes to styling these nautical-inspired shoes, there are a few dos and don'ts to live by. First up, boat shoes look great on men when paired with jeans, chinos or shorts. For women, these shoes work well with cropped or cuffed denim but also can be worn with skirts, casual dresses, shorts and khakis, too. Remember: Boat shoes are pretty casual, so the outfit itself should be casual, as well.

Another frequently asked question about wearing boat shoes is, When can you wear them? Short answer: Definitely not during the wintertime. Boat shoes are a spring- and summer-only style. Unless you live in a coastal town year round, you should probably save your boat shoes for April to September.

Now, how about where? Where is it totally acceptable to rock boat shoes and where is it...you know, not so appropriate? The general rule to follow is: casual shoes, casual events. If you work in a business-casual environment or it's casual Friday, wear them to work. Heading to the docks or on a yacht? Wear the heck out of them! Going on a casual date? Fair game! Other places to wear boat shoes include the beach, when traveling, at a casual bar, etc. But if you're attending a wedding or other black-tie event, skip them in favor of a fancier shoe like a loafer.

Best Boat Shoes

  • Sperry Men's Authentic Original Two Eye Leather Boat Shoes, $95
  • Sperry Men's Authentic Original Two Eye Nubuck Leather Boat Shoes, $95
  • Sperry Women's Angelfish Boat Shoe, $34.97
  • Allbirds Men's Tree Skippers, $95
  • Allbirds Women's Tree Skippers, $95

Are you supposed to wear socks with boat shoes?

Hard no. Do not wear visible socks with your boat shoes! We will forgive you, however, if you opt for no-show socks because it's just comfier (and less stinky) that way.

Why do boat shoes have laces on the sides?

Boat shoes actually have a long history. First invented in 1935 by New Haven, Connecticut, sailor Paul A. Sperry (does the name sound familiar?), boat shoes became a thing when Sperry cut sipes—a grip-improving groove or channel— in the tread of his shoes. The idea behind this was to provide better traction when navigating the wet decks of the boat.

In addition to the sipes, boat shoes also developed laces on the sides in order to provide a more snug fit. Because of their original design and function, boat shoes aren't supposed to slip off easily, so the side-laces were created in order to secure them well. After all, no boater wants to lose their shoes while walking across a wet deck.

Should boat shoes be tight or loose?

The original concept behind boat shoes is that they should fit tightly on the foot. When working on and navigating around a boat, you wouldn't want to skid or fall. Of course, if you're not using your boat shoes in the traditional sense, it's OK if you wear them on the looser side. Still, you probably don't want your heel to pop out the back, so use the side lacing system to make sure they're tight enough.

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