The History and Evolution of the Boat Shoe

I flew out to North Carolina and retreated to the mountains. I enrolled in a program called Restoring the Foundation. Each morning I met with a couple to guide me through my soul work. With them, I faced my deepest fears and darkest secrets.

Today, we’re going to talk about the history and evolution of the boat shoe.

Thank a dog next time you wear a pair.

Sailor Paul Sperry slipped and feel off of his boat back in the day. This led to his determination to develop a non-slip shoe. During the winter, he took notice of how his dog effortlessly ran on ice without slipping and sliding. Experimenting, he took a knife and cut notches into his shoe’s rubber sole to mimic a dog’s paw.

The result? More traction, and the invention of the first boat shoe in 1935.

Have you ever wondered why boat shoes have white soles? They were used to prevent dark scuffing marks on boats. Coupled with moccasin-style leather, the sole and the skin make up the traditional boat shoe.

In just a few years, the US Navy caught wind of this non-slipping shoe design and negotiated the right to manufacture them. Boat shoes were now ingrained into American style. It wouldn’t be long until the Kennedy family began sporting this new look.

I remember my first pair of boat shoes thanks to the Bass outlet in Branson, MO. Prep attire was still in full rage and the boat shoe became a staple, mostly because of the The Official Preppy Handbook that came out more a decade earlier. But, I wasn’t cool in the 90s at all, and I often wore that pair of shoes with socks in the winter (apparently a fashion no-no).

Last year, I picked up a pair of Sperry Top-Sider Billfish boat shoes. The Sperry brand has dominated the fraternity market for the past few years, so I finally caved in to the undergraduates’ suggestions. I wore them often, and they quickly became smelly. I’ve read Gold Bond does the trick in keeping them fresh.

This Spring, I got a pair of Jack Erwin Cooper boat shoes. From the moment I opened the box, I could tell this pair would be different than previous boat shoes. If you’ve ever ordered from Jack Erwin, you’ll notice details are important, even down to the packaging.

I opted for the Navy Calfskin boat shoes, and I’ve found I’m more careful with when and where I put them on. The look and feel is more comparable to a loafer.

Jack Erwin boat shoe

This new boat shoe design is fully making its way into the city. Maybe it’s because I’m in Los Angeles, CA, but I find myself wearing them to events and parties instead of biking by the beach.

Luxury boat shoe brands like John Lobb and Bottega Veneta are available, but they can cost upwards of $1,000.

The Jack Erwin Cooper isn’t cheap, either. With a retail price tag of $125, the look and feel is a step above the Sperry. Made in Portugal with Bologna stitch construction, they are designed to last beyond one summer. The classic style will endure too.

In short, while the boat shoe was inspired by dogs, the new breed of boat shoes are stylish and sleek; definitely not for the dogs.

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