The complete guide to men’s boat shoes

Boat shoes from Samuel Windsor

Boat shoes come in a range of colors and finishes
Image: Samuel Windsor

Do you love being on the water? If so, you’ll already know the value of a pair of quality deck or boat shoes. But these smart-casual shoes will take you to plenty of places besides the sea, river or lake.

Offering a classic, contemporary look that dates back to the mid-1930s, boat shoes are a comfortable and stylish addition to any man’s closet. To help you get the most out of yours, here’s our complete guide to men’s boat shoes.

A great American invention

Prestige boat shoes in brown leather from Samuel Windsor

Grippy rubber soles provide traction and durability
Image: Prestige boat shoes in brown leather from Samuel Windsor

The year was 1935, and yachtsman John Sperry from New Haven, Connecticut, was a man on a mission. Sick and tired of slipping about the deck of his yacht, Sperry was hot in pursuit of a solution. So far he’d tried adding emery grit to his deck paint, but the rough finish meant that any contact with bare flesh resulted in painful injury.

It looked as though Sperry was beat. But then he noticed that his dog, Prince was able to run on any surface, wet or icy, without ever slipping. He decided to investigate further and, on examining the hound’s paws, realised that the pads were covered in fine slits. Grabbing a pair of old rubber-soled shoes and his penknife, Sperry got to work recreating the pattern.

It worked! Sperry added a canvas upper and called his creations Sperry Top-Siders. A design classic was born, and today, boat shoes are popular with sailors all over the world.

Boat shoes at war

Prestige boat shoes in navy leather from Samuel Windsor

Boat shoes are ideal footwear both on and off the water
Image: Prestige boat shoes in navy leather from Samuel Windsor

I fear we have awakened a sleeping giant, and filled him with a terrible resolve,” said Admiral Isoruku Yamamoto after the bombing of Pearl Harbor. Boy was he right, and with the USA stepping onto a war footing, its rapidly expanding navy needed shoes for its new recruits.

It was boat shoes to the rescue. With their practical non-slip, non-marking soles and canvas construction, ‘Top-Siders’ looked great and were inexpensive to manufacture. They offered the perfect solution to the navy’s footwear problem and the Naval Academy soon adopted them as casual shoes for off-duty cadets.

Boat shoes through the postwar years

soft leather boat shoes from Samuel Windsor

Soft leather provides a comfortable fit
Image: Samuel Windsor

After the war, boat shoes began to evolve as manufacturers switched the traditional canvas uppers for leather and nubuck, and created the moc-toe construction we’re familiar with today.

Along with saddle Oxford shoes and penny loafers, boat shoes became essential wear for preppy college students of the 1950s. It’s a look that has never fallen from fashion – these days, you’ll find boat shoes in many different combinations of suedes and leathers. The color palette has expanded too, with boat shoes now available in browns, blues, grays and more.

Why should you wear boat shoes?

Prestige boat shoe in gray from Samuel Windsor

Lightweight and flexible – boat shoes are ideal for vacations
Image: Prestige boat shoe in gray from Samuel Windsor

For boaters, these shoes are best worn for your safety on the water. For the rest of us, boat shoes are a stylish, smart-casual option that offers a grippy, breathable footwear solution for a wide range of spring, summer and fall activities.

Heading to the country club this weekend? Reach for your khaki pants, a crisp, button-down shirt, and your boat shoes. Driving? Boat shoes give your feet plenty of feel and grip on the pedals. Travelling by train, bus or airplane? Boat shoes give your feet plenty of room to swell – there really is no better shoe for comfort, wherever you’re headed.

Looking for a vacation shoe? What better way to pack light than by opting for boat shoes? They’re practical for the beach, they’ll see you through sightseeing trips in comfort and style, and dressed up, they’re smart enough for evenings out.

Three ways to wear boat shoes

Classic boat shoe in two-tone brown leather from Samuel Windsor

Perfect with shorts and a polo shirt
Image: Classic boat shoe in two-tone brown leather from Samuel Windsor

  1. Boat shoes, shorts and polo shirt. This is a great look for the beach or boardwalk. Wear no-show socks, and if it’s hot and sunny, do remember your aviator shades and Panama hat.
  2. Boat shoes, chinos and a seersucker shirt. Perfect for sunny days, meals out, trips to the club, and more. This combination projects a laid back, classic look that’s perfect for summer.
  3. Boat shoes, blue jeans and a flannel shirt. When it’s a little cooler outside, you need an ensemble that’s warm and comfortable without leaving you overdressed. Try a pair of brown leather or nubuck boat shoes. Risk of rain? Don’t forget to spray nubucks and suedes with water repellent.

Now you know your boat shoes from tip-to-toe, it’s time to shop the look, and prepare to look dapper this season. Boat shoes really are the perfect classic footwear for men who know how to dress.

Posted in Men's Shoes.

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