Summer Shoe Series: Sperry Boat Shoe

The quintessential summer shoe.
My Sperry Boat Shoes are size
My other sizes are:
Allen Edmonds10
Red Wing9.5
Clarks Desert Boots10
Converse Jack Purcell10.5
Wolverine 1000 Mile9

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.

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 $88 or check out Sperry's site for more info.

Andrew is the founder and editor of Primer. He's a graduate of American University and currently lives in Los Angeles. Read more about Primer on our About page. On Instagram: @andrewsnavely and @primermagazine.


  • […] quintessential summer shoe. Check out Summer Shoe Series: Sperry Top-sider Boat Shoe on […]

  • Reply May 26, 2015


    Good article! The only problem is the shoe you recommended.

    I have a piece of advice, DO NOT buy the Authentic Original. They are overpriced at $88. The leather is thinner, the insole does not cover the entire shoe (it’s a half insole), and the fit is extremely tight on top.

    Instead look at and try on the Sperry Leeward 2-eyelet. The leather is thicker (more durable), the insole covers the entire foot, and it fits true to size!

    An important point I need to make is that if you want the leather lace look you can go to any West Marine store and buy a lace replacement kit!–colored-lace-kit-tan–15222870

    • Reply May 27, 2015


      Hey Steeps, Thanks for the comment and links! This has actually not been my experience at all. I love the Authentic Original and found the quality to be what I expected. The Leeward has a chunkier sole than I’d prefer, but maybe some readers will like that. Thanks again!

    • Reply March 19, 2016


      Totally agree.

      Leewards are indestructible. Full insole is the key. AO’s are nice, but the Leeward is the best.

  • Reply May 26, 2015


    Could you wear these in a casual office? I usually wear jeans and a t-shirt, but in the summer sometimes switch to shorts and a polo when it’s really hot. Would boat shoes be ok then?

    • Reply May 26, 2015


      Absolutely! If folks are wearing t-shirts, then boat shoes would be more than appropriate.

  • Reply May 26, 2015


    My go to shoe in the summer. I’ve got the Authentic originals in dark brown and I wear them all the time. I’m thinking about picking up a pair of camp mocs for the summer too, a similar style shoe.

  • Reply May 26, 2015

    Dan McKeown

    I used to subscribe to the thought that these were “old man loafers that I’d never be caught dead in.” I’m happy to say I’ve since grown out of that and now wonder how I’ve gone this long without them!

  • Reply May 27, 2015


    Great article. I think you should link some Get-Ups to this article that include Sperry Top Siders with them.

  • Reply May 27, 2015


    I’ve always loved Sperry’s – as long as I don’t have to walk much. But here’s the problem: if I have to walk more than a few blocks, or stand on my feet for a while (going to bars, catching a ball game – pretty much any activity aside from sitting on my rump) my feet and heels end up aching within an hour. The Sperry’s with clunkier soles, while significantly more comfortable, look…well, like something my grandfather would wear.

    For other folks with this problem, I recommend the Sperry Gold Cup series. At $155/pair, they’re almost twice the amount of regular Sperry’s. However, they come with a memory foam coating on the sole, and look exactly the same as the classic Sperry’s (made in the classic color combos and some of the more eye-catching ones). Sperry’s look great with just about everything outside the office, so the extra money will be worth it. (Note – I bought my first pair recently, so am not able to comment on how well they hold up – I’ll return in a few months and comment on durability.)

  • […] Summer Shoe Series: Sperry Top-sider Boat Shoe […]

  • Reply May 28, 2015

    Ella Bing

    I hardly wear socks…i typically go the gold bond route…but i’m gonna try the bag in a freeze trick…if that works, you are my new hero #ownerofstinkyshoes

  • Reply May 28, 2015


    What color are these I can’t seem to find them

  • Reply May 31, 2015


    Did anyone else experience some blisters from the back of your foot? I remember the first time I bought a pair of Sperry’s, I chose the right size but it took a little while to break in the shoe from the back. Any thoughts, ideas, suggestions?

    • Reply June 5, 2015


      Yep, this is very common. Once you get past that part they’ll be your favorite shoes.

  • […] Summer Shoe Series: Sperry Top-sider Boat Shoe […]

  • Reply June 3, 2015


    i’m sorry but im sooooo over boat shoes!!! thats the only shoe i see on primer!! im 24 and have never been a fan of them, please im sure there is way better shoes for summer than these. They alway remind me of some old preppy white guy. please do more “minimalist” styles instead of all this muchos colores clothing and shoes!! young guys don’t really dig this stuff dude!! i use to love primer but the sense of style now is just eh.

    • Reply June 20, 2015


      I’m the same age as you and I wear my Sperrys all the time. They’re the most comfortable pair of shoes that I own.

    • Reply August 12, 2015

      Mark Myers

      I’m a bit older than all of you, and I agree with G. I was a kid in the 80s and a teen in the early 90s when first Sperrys and then Bass Weejuns, both worn without socks, were all the rage, year round. Our feet were cold in winter and hot and sweaty in summer, and tended to get discolored and nasty toe jam. Wearing shoes, especially leather ones, without socks sucks. Plus Sperry Authentic Originals offer no support whatsoever. And then long after Sperrys stopped being popular with young people, dads and granddads kept wearing them. For people my age at least, they will always be tainted by this. They are the footwear equivalent of the Member’s Only jacket (with which they were commonly worn.) And now because of their faddishness, Sperry has jacked them up WAY above what they cost back in the 80s, even adjusted for inflation. NOT worth it.

      • Reply March 20, 2018


        The late 80s and throughout the 90s I also wore Sperry’s all the time. I still own a pair today. Yes, I do remember during hot and humid days the shoes would feel slimy from all the sweat retaining in the shoe. Nevertheless, these shoes were comfortable. No one thought about wearing socks at that time on boats or not on boats while wearing these shoes. Sperry now sells no show socks of their own. Their is a product called Gekks that can be placed in the shoe also. Most no shows will do. Wearing these socks helps in controlling the moisture level and “slim factor”.

  • […] | Shorts: J.Crew Factory, $20 | Watch: Brathwait, $185 | Sunglasses: Cheaters, $11 | Boat Shoes: Sperry, $88 | Sneakers: Adidas Stan Smith, […]

  • Reply August 6, 2016

    Jake Holden

    This is an amazing article! I’m only 17 and I’ve read dozens of your articles and almost live by them! I was wondering if you knew what kind of Sperry Boat Shoes you have? I love the look and color and would love if you could let me know. Thank you so much and keep on writing!

  • Reply February 16, 2018


    Great post! thank you for sharing
    Please do share some more

  • Reply September 12, 2018

    Josh Houghton

    I have a pair, but been struggling to find a pair that doesn’t rub the back of my heel really bad. Right now I’m wearing a 9.5 and it feels good, but even with no show socks it rubs my heal. Would you recommend going down a little or going up?

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