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boat shoes history men
boat shoes history men

Style Defined: Boat Shoes

June 8th, 2016

Comfort, style and nautical appeal… What’s not to love about boat shoes?

Boat shoes have long been a men’s summer shoe staple. They’re part loafer, part sneaker, part beast of their own – and proven over the years to be nothing short of a crowd pleaser.

Also called ‘deck shoes,’ boat shoes are usually constructed with canvas or leather moccasin-style uppers. By far the most popular iteration is a classic mid-brown leather upper with a contrasting white sole.

Beyond that, as you look further into the physical makeup of the shoe, the purpose and functionality becomes clear.

boat shoes history men

First, the characteristic rubber sole is unique from the soles of sneakers or other casual shoes. The most important and defining aspect of these soles is that they are non-marking.

Sailors, despite their reputations for dirty mouths, keep a clean ship. Anything else is a safety hazard and an eyesore. So naturally, a sole designed for a boat will be inherently resistant to scuffing up that pristine deck.

Additionally, the soles have a built-in safety aspect – they’re designed to be slip resistant. This is an extra-important quality for folks regularly walking around on sea-spray covered surfaces.

boat shoes history men

In fact, legend has it that Paul A. Sperry got the idea to develop the signature sole after a nasty spill on his own boat. He then noticed that his dog, Prince, was trekking around just fine.

After inspecting his dog’s paws, he noticed herringbone-like grooves. Inspired, he created soles with similar siping that replicated the effect. He’d later go on to found Sperry Top-Sider, the de facto go-to boat shoe brand.

Other defining features of boat shoes include metal eyelets on either side of the shoe that help drain water and keep the footwear from becoming waterlogged.

Additionally, the laces are usually leather, which makes them easier to work with when wet, rather than cloth laces that are impossible to untie when wet.

boat shoes history men

| BRIAN WEARS | Blazer c/o Tommy Hilfiger, Brunello Cucinelli shirt, J.Crew chinos, Oliver Peoples sunglasses, Rolex watch, Boat shoes c/o Jack Erwin | PHOTOGRAPHY | by Rob McIver Photo

Now, guys love boat shoes for a variety of reasons. One is that the soles are soft and comfy as all get-out, as they are designed for grip rather than durability.

Another is that they are easy to wear. No lace-tying required but a bit more functional than a loafer.

Yet another is that functionality itself, as men tend to be drawn towards clothing and footwear with a purpose, whether they use it for that purpose or not.

And last is simply that sometimes unexplainable, but always irresistible, nautical appeal. For the same reason we love navy and white stripes, we will always love boat shoes.

Like other nautical gear, there’s somewhat of a preppy aesthetic that goes along with them, but as years pass they’ve spread more and more into the mainstream and are now widely worn by gents of all sorts.

boat shoes history men

As for styling, it’s important to remember that they are a casual shoe. I was at an appointment the other day and my doctor walked out of his office in a full business suit, tie, and boat shoes. No way around it, it just looked wrong. Terrible, actually.

Sure, the leather versions are a bit more put together than an athletic sneaker, but not by much. That said, they’ve got a helluva lot more class than a running shoe, and are a great summer substitute for your CDB’s in your chino-and-OCBD casual uniform.

boat shoes history men

The best part is that they look better and better as they age, not unlike a good pair of raw denim. Take your pick from the requisite high-street brands like Sperry or Eastland, or go high-end with some Yuketens or Rancourts (both USA-made, FYI), and flaunt your nautical inclinations with pride.

Thanks for reading.

Stylishly Yours,

Adam Lehman
He Spoke Style

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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