How To Wear Boat Shoes (Looks & Styles)


Boat shoes are extraordinarily versatile and can be worn with just about anything. Compared to sneakers, they add extra class to any outfit, whether it’s shorts and a t-shirt or a full blazer and tie combo. The appeal of boat shoes lies in their versatility. They look just as good boarding a plane as they do walking into your favorite happy hour spot after work.

General Rules

There are some ground rules (more like suggestions) for wearing boat shoes. Own your style, but it never hurts to have a little expert advice.

  • Don’t wear them with athletic wear. While the athleisure trend is very popular, athletic wear doesn’t pair well with leather shoes. Swap your sweatpants for a classic pair of jeans or shorts, depending on the temperature.

  • Keep your ankles free. The beauty of boat shoes is the open-top, which is cooler in the spring and summer. To maintain airflow to the feet, ankles, and legs, add a cuff to jeans or pants, or have them hemmed shorter. Shorts are also an easy way to show off your favorite boat shoes. 

  • Don’t wear boat shoes in the winter. The same open-top construction that makes boat shoes great for the summer makes them dreadful in the winter. Don’t be afraid to retire your boat shoes when the weather calls for it. You’ll get to wear them again soon enough.

Pick The Right Shoe

There are A LOT of boat shoe variations, available in dozens of colors and different materials/textures. A classic brown leather boat shoe is extremely versatile and will go with almost anything, but don’t be afraid to experiment with other styles and colors too. Sometimes you might prefer a playful color to put you in the vacation state of mind. 

Casual Looks

To assemble a classic, casual look, pick a pair of shorts in a solid color and wear them with a polo shirt or short sleeve button down. Alternate with a t-shirt for an even more casual look. A long-sleeve button-down (with the sleeves rolled up) can be swapped in for a little extra class. For a low-key look, pick shorts that are khaki, navy or light gray in color. Jeans or chinos are a great alternative if the weather is cooler. Keep it extra casual and don’t tuck your shirt in - this is the perfect time to embrace a more laid-back look.

Summer Looks

Summer looks are usually light (both in material and color) to stay cool in direct sunlight or high humidity. For a more vibrant style, pick a more colorful pair of shorts. Salmon, light blue and turquoise are all popular summer colors. Pair with a complementary top, but avoid color clashing (like salmon shorts and a turquoise shirt). Keep it simple and classic with one bold color and the rest of your outfit relying on balancing neutrals. To get that classic New England look, consider shorts or a shirt with a nautical pattern (think lobsters, anchors or sharks).

In the hottest temperatures, avoid cotton shirts and go with a moisture-wicking synthetic material that will draw sweat away from the body. Keep shirts untucked for extra airflow.  

Cooler Weather

Boat shoes can still be worn in cooler temperatures when paired with the right outfit. Ditch the shorts in favor of jeans or chinos, depending on where you’re going. Jeans are a little more casual but can still be dressed up with the right shirt. Complete the casual look with a T-shirt and a bomber jacket. Ready to take your outfit to the next level? Replace the T-shirt with a button-down and consider taking a blazer out for a spin. For a classic nautical look, go with a button-down and a sweater or fleece vest over top.

Looks & Outfits For Formal Events

You can wear boat shoes in more formal settings, with some important exceptions. Boat shoes shouldn’t be worn to black tie events, or with tuxedos, but they can be worn to all kinds of other events.

Just a little formal: Pair boat shoes with chinos and a collared shirt (short sleeve or long sleeve).

A little more formal: Keep the chinos and collared shirt, but add a sweater or a blazer.

A lot of formal: Go with the boat shoes, chinos, button-down, and blazer look, and add a tie (traditional or bow-tie) if you’re looking to make an impression.

Date Night

For date night, grab a pair of jeans or chinos and pair it with a polo shirt or short sleeve button down. Stick with a collared shirt - T-shirts are a little too informal. If the weather is cooler, consider adding a light jacket or blazer.

Should You Wear Socks With Boat Shoes?

It’s really up to you. Wearing boat shoes without socks is more conventional, but there are no-show socks specifically designed to be worn with boat shoes. It’s your personal style, and so make it your own and wear what feels right. Read more about whether you should wear socks with boat shoes.

Shop Boat Shoes From Samuel Hubbard


Thinking about a new pair of boat shoes? Check out our collection! Samuel Hubbard boat shoes are designed to go anywhere and everywhere that you do. We believe that empowering others for their journey starts from the ground up. Handcrafted construction from the finest materials means all-day comfort wherever you go.