Summer Shoe Series: Sperry Boat Shoe

My Sperry Boat Shoes are size
My other sizes are:
Allen Edmonds 10
Red Wing 9.5
Clarks Desert Boots 10
Converse Jack Purcell 10.5
Wolverine 1000 Mile 9
Chippewa 9.5

For many a gentleman, that moment in spring when it has become clear the wool, herringbone, sweaters, and heavy selvedge denim are no longer appropriate is one of denial and then fear. See, dressing in the colder months is easy, just simply keep adding things until you look rakish and put-together, but summer — summer is an entirely other mistress, one that demands calculated, intentional choices to create a well-dressed finished product with the least amount of items possible.

But this fear of a more minimal aesthetic is misguided anxiety – the real gift of summer style is the advantage of stepping back and focussing on only a few, flexible basics.

Case-in-point: Footwear, and the blessing and convenience of the boat shoe. Wear it with trim fitting flat-front shorts and a polo and you’ve got a versatile getup you can rock at almost every summer event. Pair them with slim chinos and a button-up and you have summer-ready business casual. Ditch the button-up for a short sleeve henley and now the chinos and boat shoes form a casual but intentional warm weather look that fits in whether you’re in preppy New England or hipster Venice.

If you’re a young guy just getting your foot in the door of being better dressed, you may see the boat shoe and cackle that they’re old man loafers that you’d never be caught dead in. But the fortunate reality is the boat shoe has become synonymous with essential summer shoes, whether you’re preppy, casual, or anything in between. Just because you think your unstylish dad wears boat shoes, doesn’t mean boat shoes are unstylish because your dad wears them. In fact, as essential as the white canvas sneaker is to summer wear, the boat shoe reigns number 1 by a huge lead.

When it comes to picking a boat shoe, there are no shortage of options, but you can’t beat the original: the Sperry Boat Shoe. Paul Sperry was an avid sailor who almost lost his life when he lost traction while navigating the deck of his boat. Prior to the boat shoe, sailors wore smooth soled shoes, which would lose grip when walking on a wet deck, or worse they would go barefoot to gain an ounce more of stability. One winter, Sperry was intrigued as he noticed his pooch Prince was able to run across the ice without slipping. He hypothesized the cracks in Prince’s paws enhanced his traction.

Inspired, he cut slits into the bottom of his rubber soles in a herringbone pattern. Similar to how tire tread works, Sperry’s modified shoes made an incredible difference and the boat shoe was born. The first model was made of canvas, and the leather boat shoe we know today debuted in 1938. In 1939, the navy contracted with Sperry to produce them for sailors.

Bottom of original Sperry boat shoes

The boat shoe’s early life was one of function, but with the increased national interest in New England Prep in the 60’s heralded in by JFK introduced the boat shoe as a style staple. By the time “The Official Preppy Handbook” was published in 1980, the boat shoe had become synonymous with essential summer wear regardless of personal style.

How to Wear Them

Boat shoes are the grown man’s answer to flip flops or sandals. They can be worn to the beach or the pool, but unlike flip flops, can be worn in situations that require a higher level of dress like your boss’s bar-be-cue and most summer dates. Like sandals and flip flops, boat shoes should always be worn with a sockless look. Why? It stems from their functional history: Sailors working in wet conditions would obviously not wear socks, since they’d become a spongy, uncomfortable mess.

When wearing shoes sockless in hot and humid conditions for long stretches at a time, things can get really funky, really fast. To keep things fresh there are several things you should do.

Boat shoes get a little smelly? Put them in a ziplock bag and place them in the freezer. The cold will kill the odor-causing bacteria.

First, only wear your boat shoes when you have clean feet. Socks act as a buffer between your feet and your shoes, and are the first line of defense against sweat and odor-causing bacteria. Without socks, all that nastiness is going right into your shoes. If you’re rushing back from a long day, ditching your socks and slipping on your Sperry’s would be a fast way to shortening their lifespan.

Second, combat sweat by using a body powder like Gold Bond, or a foot spray. These will help control sweat, as well as offer a scent. Deodorant for your feet, essentially.

Third, I used the term “sockless look” intentionally: The goal is to look sockless, but if the idea of wearing shoes without them disgusts you to no end, you can go for no-show socks that are designed to cover the foot without peaking out of the shoe opening. There are a ton of options available that won’t break the bank.

no show socks

And finally, just like your dress shoes, you shouldn’t wear them day after day without a break. By rotating your footwear, it allows the shoes to fully dry, which keeps them odor free but also helps maintain their shape.


Since these are loafers and we won’t be wearing thick socks (or any at all) we need to keep that in mind when choosing the right size. You’ll want to size down until they’re snug, so they don’t slip and cause blisters. The perfect fitting boat shoe should fit and be comfortable like a glove.

Shown here in tan, pick up a pair on Amazon for $65 or check out Sperry's site for more info.

This post may contain affiliate links, read about our editorial promise
Andrew Snavely

Andrew founded Primer in 2008 and brings 15+ years of men's style expertise. Known for his practical, relatable approach to style and self-development, he has been a recognized speaker at conferences and has styled work for top brands. Off-duty, he loves photography & editing, and enjoys road trips with his dog, Leela. Raised in rural Pennsylvania, educated in DC, and living in LA for nearly 20 years, Andrew's diverse experiences shape the relatable and real-world advice that has helped millions through Primer. On Instagram: @andrewsnavely and @primermagazine.