8 Sperry Boat Shoes (and More) for Men Who Don't Like to Fall Down 

Sperry creates non-slip, sea-worthy, and preppy-approved shoes for men.
IMAGE Instagram/ sperryph

Style pundits make the case for having seven styles of shoes for men, one of which, depending on who you ask, should be a boat shoe by Sperry. 

The American footwear company, which celebrates its 85th anniversary this year, gave humanity the gift of the Top-Sider, the world’s first boat shoe. It was explorer, sailor, and inventor Paul Sperry who founded the company in 1935, and we’re sure he’ll be glad to know how his company has stayed true to its course, even after eight decades (and a raging pandemic).

Like a boat moving through the great unknown, Sperry continues to build on its mission to create sea-worthy, non-slip shoes (Paul’s unfortunate fall into the waters led to its invention) that are now considered a staple in a man’s wardrobe—even if he doesn’t know the difference between starboard and port or rarely steps into a seafaring vessel.

Admittedly, the boat shoe is not our most favorite footwear style, but we do recognize the appeal. The Official Preppy Handbook anoints the Top-Sider as integral to the fashionable by putting it on its cover. And, yes, wearing the shoe does have that magical quality of denoting blessed leisure, the kind filled with white sands, all-day drinks, and no obligations.

It may be the easiness of wearing it, the non-slip technology (turn over a Sperry to find its signature wavy etch marks), or just those loopy leather ribbons that make the boat shoe feel that way. Whatever it is, it’s a good idea to have a pair (or three) in your closet. Below, some of the best Sperry shoes for men to consider.



Gold Cup Boat Shoe

Photo by Sperry.

Start with a big boy. Obviously, this unit from Sperry’s premium Gold Cup collection is not your average boat shoe. Full-grain leather and a lambskin lining set this apart from the rest. Also, it’s just huge (that’s what she said). If you’re going to commit to a boat shoe, why not do it with something different.


Gold Cup Handcrafted in Maine 1-Eye Camp Boat Shoe

Photo by Sperry.
Recommended Videos

As its name boasts, this is hand-made in Maine, the American state known for rocky coastlines and fat lobsters (hence, its inhabitants need reliable boat shoes). The more subdued appearance is the result of oiled leather, which remains sturdy even when exposed to saltwater.


Authentic Original 2-Eye Plush Varsity Boat Shoe

Photo by Sperry.

The Plush Varsity, says Sperry, is 40 percent lighter but still as reliable as previous versions. Note the insole adorned with collegiate stripes—not only does it double down on the preppy feel, but it also makes the shoe comfortable.  


Authentic Original 2-Eye Bionic Boat Shoe

Photo by Sperry.

If you are a friend of Mother Earth and live by the code of doing as little harm to the planet as possible, turn to the Bionic series of Sperry shoes for men. The eco-friendly boat shoes are made with yarn and fabric spun from plastic that is recovered from marine environments. On average, each pair is made from five recycled bottles. Good to know: The design of this boat shoe is inspired by the uniform of the U.S. Navy, which—also good to know—incorporated the Top-Sider as its official footwear for casual occasions.


Men's Captain's 2-Eye Sneaker

Photo by Sperry.

Is it a sneaker as the brand calls it or a boat shoe as it appears? Why can’t it be both? If you are a white sneaker fanatic, you’ll be pleased to find that Sperry’s original 1935 design has been reimagined into a crispy white boat shoe.



Men's Captain's CVO Sneaker

Photo by Sperry.

So, yeah, the brand known for Top-Siders has other styles, too, including this no-frills canvas sneaker that you can wear to death on weekends.


Men's Captain's Slip-On

Photo by Sperry.

Similarly, there is a slip-on style that you can slip on in case laces are never your thing.



Gold Harpswell Driver

Photo by Sperry.

Finally, here’s a dad-style driving shoe. Tired feet will appreciate its built-in ASV tech, which promises to reduce the effect of shock (maybe Dad jumps a lot?). Do you know who likes this? Crooner John Legend, who includes the shoes for men in his edit for Sperry. We can see the cardigan-wearing singer in this, really.

View More Articles About:
More Videos You Can Watch
About The Author
Clifford Olanday
Editor in Chief, Esquire Philippines
View Other Articles From Clifford
Latest Feed
Load More Articles
Connect With Us