If nautical nuisance be something you wish – keep looking! The boat shoe is nothing to mess around with. First designed by sailors for sailors in the 1930’s, the shoe featured a special grip on the outsole, which helped many a matey find his sea legs. Today, the boat shoe (also called a deck shoe) has been given new life. Riding a wave of recent revival, the boat shoe is solidifying its place as an American classic. But many are clueless on how to wear boat shoes. Fear not, matey! Our “how to wear a boat shoe” guide will have you looking best on the deck.

How to wear boat shoes


1. Throw The Socks Overboard

Yes, we realize this is a hotly contested point. But you’re here for our opinion on how to wear boat shoes and here it is: never with socks. The original captains that toted these now-classics didn’t wear socks with them and you shouldn’t either! Albeit, the sailors of yesteryear were more concerned with practicality than fashionability – because what’s the point of wearing socks on a boat? – the verdict still stands.

How to wear boat shoes

You’ll walk the plank for that one!

Now, the boat shoe pioneers anticipated their feet getting soaked with seawater. Your feet? With no socks, they might get wet with something else – sweat. If this is a problem, try using cotton inserts, which are designed as sock substitutes to be worn inside the shoe, underneath the sole of your foot. They absorb sweat and dirt and are usually even machine washable. If not these, then try out some invisible socks, which sit much lower on the foot than ankle socks. If all else fails, don’t be afraid to sprinkle some foot powder in your boat shoes.

How to wear boat shoes How to wear boat shoes                 how to wear boat shoes - docksiders

Tommy ‘Arlington’ Boat Shoes             Maine New England Red suede boat shoes           Dominick Colorblock Boat Shoes


2. Bare Ye Legs!

So why the strict no-sock policy? Here’s all you need to know on how to wear boat shoes: it’s all about the legs, baby. With no socks covering your ankles, there’s more leg to show off.

how to wear boat shoes

L.ANDSAILING - Boat shoes - red    L.ANDSAILING - Boat shoes - navy    L.ANDSAILING - Boat shoes - black

Lacoste L.ANDSAILING – Red                  Lacoste L.ANDSAILING – Navy                Lacoste L.ANDSAILING – Black

Boat shoes are the pinnacle of prep style, so prep it up as much as your heart desires. Pick out some above-the-knee shorts to go with your boat shoes. Next, you’ll want something long-sleeve. Try a sweater if weather permits, or else a polo shirt and cardigan, or a simple button-down. This style glimmers under the sun, so wear it to the beach or out on the water  and flaunt your calves.


3. Maritime Business

You might be wondering how to wear boat shoes in a less casual setting. The original deck shoes only came in light and dark brown leather. Choose this style for a business-casual look that goes great with khakis or chino pants and a button up. As long as your office isn’t too stuffy, boat shoes could even suit your workplace attire. Don’t get too carried away though – boat shoes should never be worn with dress pants or to a formal occasion such as a wedding. The rustic leather deck shoe may be a bit dressy, but still quite far from a dress shoe!

how to wear boat shoes

.                                         How to wear boat shoes How to wear boat shoes

Timberland Classic Boat Shoe               SPERRY Tan leather boat shoes


There you have it, show off your legs or show off to your boss. Just never with socks! The boat shoe is a versatile classic fit for many occasions.

What do you think? Did we miss anything? Let us know in the comments below!