Boat Shoes Explained: History, Style, & How-To Guide

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Once the epitome of preppy leisure wear, the overall shift towards relaxed dressing means the boat shoe is now in ever-increasing demand by everyone who wants to stay comfortable and stylish in relaxed settings. Explore the heritage and characteristics of this iconic style in our boat shoe guide.

Boat Shoes: The Video Guide

Get ready to set sail around the globe, or at least around the specifics of the popular nautical-inspired white sole shoes we all know as the boat shoe! Raphael is on hand to guide you through the intricacies of this preppy fashion staple to ensure you always look “boat cool” whenever you wear a pair.

What Makes Boat Shoes Special? Boat Shoe Characteristics Defined

The boat shoe, also known as the deck shoe and top-sider, has followed the well-trodden path from being purely work/utility wear to becoming a truly classic piece of men’s footwear (and women’s, too). In 1980, with the publication of The Official Preppy Handbook by Lisa Birnbach the boat shoe began to be identified as an essential and integral part of preppy styles. Boat shoes, however, are not just restricted to preppies but have been adopted by a large number of people and are a staple in many wardrobes. Due to their unique design and construction, they are not just great for boat decks but the perfect footwear for summer months.

Boat Shoe Characteristics

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Boat Shoes are known for their Moccasin Toe Construction

Moccasin Toe Construction

One of the most distinct parts of a boat shoe’s makeup is the moccasin style toe. The puckered stitching resembles that of an apron like you might find on another preppy fashion staple, the penny loafer. However, boat shoes feature a more rugged looking moc-toe.

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Boat Shoes are unusual as they have 360 degree lacing

360 Degree Lacing System

Traditionally, boat shoes would feature long laces that fed through eyelets near the ankle and heel of the shoe before being laced and tied like a regular Derby shoe. The purpose of the 360 degree lacing system is to lock the foot into the shoe to ensure a firm grip in rough waters. Nowadays, the lacing at the sides and back is decorative and separate from the functional laces.

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Boat Shoes feature a Derby closure

Derby Construction

As you would expect from something within the casual category of footwear, boat shoes lace in the Derby style. This open lacing system allows for a greater range of adjustment and well as increased ease when putting the shoe on or taking it off. This also helps define the shoe as something other than a formal Oxford style.

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Boat Shoes use thick leather laces

Thick Leather Laces

Unlike other types of footwear, boat shoes are laced with strips of leather, often in white as part of the shoe’s coastal identity. Waxed cotton laces may be king when it comes to more formal footwear styles, but these laces simply wouldn’t survive well for the more practical purposes of a boat shoe.

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Boat Shoe soles are a defining feature

Special Soles

The iconic white soles of a boat shoe are traditionally non-marking and bear a unique pattern to improve grip on slippery surfaces.

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Boat Shoes have a special stitched heel

Heel Stitching

At the heel of a boat shoe, you’ll find that the heel has been pinched and stitched in a horizontal line, mimicking the moccasin toe. This line of stitching is to create shape to the heel cup without having to resort to using several intricate pieces of leather like you would see on a regular dress shoe.

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Boat Shoes use unlined leather in their uppers

Unlined Leather Uppers

Part of the practical nature of boat shoes dictates they should be comfortable and flexible. This means many traditional boat shoes are in fact unlined, so they can remain supple and provide a light feel when worn.

The History of Boat Shoes

Before the advent of the modern boat shoe, sailors and boatmen alike struggled to maintain a firm foothold on the slippery decks of their boats. For many years, frequent accidents were the norm, making Jack Sparrow look somewhat competent!

Sperry & the Herringbone Rubber Sole

In the early 1930s, an ardent sailor, Paul Sperry, was struggling with this problem in his everyday life. One winter day in Connecticut he took his dog, a cocker spaniel named Prince, out for a romp and was amazed by Prince’s grip while running across ice. The traction he managed to generate on the slippery surface intrigued him.

Sperry figured that it had something to do with the pads of Prince’s feet. Upon closer examination, he realized the natural cracks and grooves on Prince’s paws formed a herringbone-like pattern that gave him grip while on the ice. Sperry then hit upon the idea of cutting similar patterns on the soles of the shoes he used while boating.

The natural grip in his dogs paws is what inspired Paul Sperry to create the Boat Shoe

Paws for Thought

Inspired by his dog’s solid performance on the ice, Sperry realized the natural grooves on the dog’s paws were the key to anti-slip success. Adapting the design for human footwear, boat shoe soles look flat at first but once flexed, you can see how the grooves open up to increase traction. It’s this action that provides grip in slippery situations much better than other rubber-soled footwear such as a running shoe or even Crocs.

Siping, the U.S. Navy & U.S. Rubber Company

Sperry’s discovery already had a name, however, as the concept of splitting or siping the sole of a shoe had already been invented and patented in 1923 by John F. Sipe. Sperry used the same process, and his design was successful in increasing the traction of shoes on a boat’s surface.

Unfortunately, his black-soled boat shoes left unsightly marks on the boat’s deck, a major flaw. With renewed focus, Sperry tested a few more options and quickly realized that white-soled shoes didn’t leave any visible marks. So in 1935, he introduced the Sperry Top-Sider shoe with mid-to dark-brown leather uppers and a white rubber sole, with the bottoms cut in a trademark herringbone pattern. After this final modification, his shoes gained momentum and became the next big trend among sailors and boaters but remained a niche product.

A Vintage Sperry Topsider Ad Showcasing the Unique Rubber Soles

Stable Sailing

Although not initially apparent to non-nautical folk, the name “Top-Sider” comes from the fact that Sperry’s shoes were designed to keep you on the top side of your boat. A major statement about the shoe’s abilities, but it’s been the mainstay of Sperry’s appeal to audiences for decades.

In 1939, the U.S. Navy recognized the benefit of the new shoes and negotiated a deal to manufacture Top-Siders for its sailors. Eventually, Paul Sperry sold his business to the U.S. Rubber Company, which started to market Sperry Top-Siders throughout America under the Sperry brand.

A Vintage Sebago Docksider Ad

Going Dockside

Another term used to describe boat shoes is “Docksides” or “Docksiders”. While the term originated with Sperry’s famous shoes, the name is now used to describe pretty much any brand or style of boat shoe. This makes it interesting, as you could be using the same name to describe a shoe sold by either Walmart, Tommy Hilfiger, or Prada!

Boat Shoes FAQ

What is special about boat shoes?

The most unique feature of boat shoes is their distinctly scored or “siped” soles. This allows you to maintain grip while on slippery surfaces, such as the deck of a boat.

What makes boat shoes different?

There are several defining characteristics of a boat shoe, from the unlined leather upper, moccasin toe, and 360-degree lacing. But it’s perhaps the unique siped soles that open when flexed in order to give you a better grip on slippery surfaces.

Why are they called boat shoes?

Boat shoes get their name from the fact that they were created to be worn on boats. As the deck would become slippery with water, sailors needed a shoe that would keep them top-side. Thus, the boat shoe was designed by Paul Sperry in the early 1930s.

Are boat shoes meant to get wet?

As the name might suggest, boat shoes are intended to stand up to wet weather conditions. While it’s never a good idea to expose leather shoes to prolonged periods of wet conditions, the oiled leather uppers of a boat shoe make them harder wearing against water than a standard dress shoe.

Are you supposed to wear socks with Sperrys?

Sperry’s, or indeed any brand of boat shoe, can be worn either with or without socks. Traditionally, they would be worn without socks, but it’s entirely down to your own tastes as to how you wear yours.

Is it ok to wear socks with boat shoes?

Boat shoes can be worn with socks if you wish, but it pays to get them right. A pair of multicolored “crazy” socks can look a little juvenile with boat shoes, just as thin black dress socks can look like a formality clash. Coordinate your trousers, socks, and shoes well, and use a pair of no-show or ankle socks when in doubt.

Do you need boat shoes for a boat?

Although not strictly necessary while boating, a pair of boat shoes makes your boating experience all the more authentic. It’s worth noting that if you’re looking to engage in professional or extreme water-based activities, boat shoes may not be the right choice for you. However, for casual boating excursions, a pair of boat shoes is a fine addition.

Why do people wear boat shoes on a boat?

Boat shoes are worn due to their specially designed soles that provide extra grip. Inspired by his dog’s paws, Paul Sperry cut grooves in his shoes’ soles to improve his grip while at sea. With some development, the boat shoes we see today are largely unchanged from their original design.

Classic Vs. Modern Boat Shoe Styles

Having previously outlined the characteristics of classic, traditional boat shoes, it’s worth noting that there are many variations on the style offered by affordable to high-end retailers including Polo Ralph Lauren to the Italian luxury company Loro Piana.

Similar to the boat shoe style, find out if this $1,000 loafer from Loro Piana is worth it in our in-depth review.

Some purists only wear either the Sperry Top-Sider; either the Original Boat Shoe in Classic Brown or the Billfish 3–Eye in Dark Tan, or the Quoddy Men’s Boat Shoe as these styles most resemble Paul Sperry’s original design. However, there are a variety of high-quality manufacturers who offer comparable models.

As previously alluded to, the boat shoe style is also a favorite of the high-fashion world, and many a strong luxury fashion player has turned their hands to creating styles for their collections. The waterside heritage and association with wealthy folks who can afford yachting holidays have created a desire for the understated luxury look at many price points, thus contributing to a healthy portion of the footwear market share.

Recent years have seen all kinds of unique color combinations for boat shoes
Recent years have seen all kinds of unique color combinations for boat shoes

While leather – specifically nubuck – is most associated with traditional boat shoes, they are available in many different styles, materials, colors, and finishes. It’s without a doubt there’s been a recent push toward creating new updated styles for each passing season, but it can be easy to get carried away. Our advice is to stick closer to traditional models for the best bang for your buck.

How to Master the Boat Shoe Style

Apart from the obvious, when out boating, boat shoes can be worn in a variety of ways. In everyday wear, they can easily replace your sneakers and loafers, but shouldn’t be seen as a replacement for more formal styles like an Oxford.

Best Jackets for Boat Shoes

When it comes to boat shoes, it’s best to avoid structured jackets such as orphaned suit jackets or sports coats with a strong silhouette. A blazer may work due to the nautical association, but it’s generally an advisor to skip bold tailoring for the risk of looking too stuffy.

Raphael wears a Harrington Jacket with his Boat Shoes
Raphael wears a Harrington Jacket with his Boat Shoes

Instead, focus on soft, unstructured sports coats and odd jackets to capitalize on the boat shoe’s relaxed aesthetic. A particularly great pairing partner for boat shoes is the overshirt or “shacket”. It’s another garment that has utilitarian roots, and in blue tones can make an excellent blazer alternative in more dressed-down ensembles. You could also consider the Harrington Jacket as another great alternative here.

Best Shirts for Boat Shoes

Without a doubt, the classic white T-shirt is an excellent example of a great pairing partner when it comes to boat shoes. You could even lean into the sailing heritage by going for a striped Breton shirt.

Otherwise, avoid tailored dress shirts and go for other preppy style staples such as the classic OCBD (Oxford Cloth Button-Down), polo shirts, and potentially even a flannel shirt for transitional seasons.

Best Pants for Boat Shoes

As a classic rule of thumb, boat shoes should never be lighter in color than your pants or shorts. But recent years have seen far more creativity, allowing you to mix bolder colors together.

Perhaps most exciting is the multicolored checked Madras pattern that can be configured as a shirt, jacket or, indeed, pants. Or maybe Seersucker is more your style? Whatever you choose, these summer classics in cotton and linen fibers are a surefire success when wearing boat shoes.

Don’t forget that denim is also a happy partner to the humble boat shoe. Recently we’ve seen the comeback of a more classic cut, nothing like the skinnier fit that would have been available in a prior year. Opt for a classic, straight leg in a dark blue denim for a timeless look.

Boat Shoes pair wonderfully with denim

Going Sockless?

One point on which there has been much-heated debate is whether they should be worn with or without socks. Boat shoes were originally meant to be worn without socks for practically while boating, but in an urban setting, according to your school of thought, they should probably be worn with socks. If you are concerned that your bare feet will sweat too much, but you don’t like the look of socks, then a simple pair of ankle socks provide the best combination of style and comfort.

Boat Shoes and Knitwear

As boat shoes are usually associated with summer months, it may feel strange to consider wearing them with knitwear, but it is worth considering as there are many suitable knitwear options out there. Plus, boat shoes make a wonderful choice for transitional dressing, too.

Go for knits in a classic style – we’re big fans of a v-neck at the Gentleman’s Gazette, but a crew neck would also suit the nautical theme. Fibers like merino wool, cotton, and linen are all available as knitwear, which are some of the best for warmer weather or changing seasons.

A classic V Neck sweater pairs well with Boat Shoes
A classic V Neck sweater pairs well with Boat Shoes

Boat Shoe Maintenance: How to Care for Your Boat Shoes

Like all shoes, boat shoes need to be taken care of, especially since they are often exposed to saltwater and the sun.

Boat Shoe Care

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Saphir Cordovan Polish

Leather Care for Smooth Leather Boat Shoes

To protect smooth leather from the elements, shine them with water-based cream shoe polish on a regular basis. It’s the stuff you find in glass jars, not tins. Don’t apply hard waxes for a mirror shine, as this makes your boat shoes look too formal, and can clog in the stitching. Avoid liquid and quick-drying polishes that contain alcohol or silicone, and stick to high-quality cream polishes.

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Brass Bristle Brush

Leather Care for Suede & Nubuck Leather Boat Shoes

Suede boat shoes can be cleaned by sprinkling and massaging cornmeal onto the surface. Leave them overnight and then brush off the cornmeal. Use a brass bristle suede brush to realign the grain. Nubuck leather can be brought back to lustre using a nubuck brush. You can also remove spots using a pencil eraser and a vinegar and water solution. If you have oil or fat spots, apply rubber cement, allow it to dry and then rub it off. Again, you do it at your own risk.

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Preston creating a slurry with cold water and soap flakes.

Canvas & Other Cloth-Based Boat Shoe Care

Although some say your canvas boat shoes can be machine washed if they don’t contain any leather, I would not do it. Much better to hand wash them with soap because you may destroy inexpensive boat shoes in the washing machine. Of course, don’t use any sort of polish on your canvas shoes!

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Balled Up Newspaper Helps to Keep your Boat Shoes Dry

What To Do With Wet Boat Shoes

Dry your shoes at room temperature and avoid direct heat or sunlight to prevent them from drying out and developing cracks. Stuffing them with newspaper can help retain their shape when wet. Brush them when dry, and apply shoe cream if required.

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Luxury Travel Shoe Horn Handmade

Practice Good Daily Care

Always use a shoe horn to put them on and maintain the shape and structure of their backs. Keep them free of dirt, dust and salt deposits and use a brush to do this as required. Store them carefully, using shoe trees to help retain their shape. And don’t forget to keep a close eye on their soles and get them repaired when you see significant signs of wear and tear

Reader Comments

  1. One of my most favorite shoe styles from earlier days; though I must confess to having turned to loafers lately.
    Presently I have one pair only in marine inspired hues; Camel Active in a combination of off-white nubuck with navy blue leather, worn last year on an evening cruise.
    Your expectedly well-researched and written article though entices me to put them together tomorrow with new white Pal Zileri jeans and a light blue Ralph Lauren button-down; for Eid festivities

    1. Buenas tardes Raphael un saludo efusivo desde las palmas de gran Canarias como siempre tus artículos y minuciosidad son casi arqueologícas siempre hago participe de los mismos a mis compañeros y amigos habiendo de nuevo el debate al respecto de nuestros calzados náuticos, Raphael de nuevo mil gracias tu seguro admirador : Roger Domínguez y Flore

    2. I have a brief comment on the evolution of the boat shoe. Boat shoes from 15 or more years ago often had a drainage hole by the instep to the shoe. In many boating situations, your feel get wet, the shoe fills up with water, and some means of drainage is needed. The newer shoes that I have seen omit this drainage hole. It seems as if the newer shoes are made for fashion, not for boating. I feel that something has been lost.

  2. I would never wear socks with topsiders, especially white ones. I use them from May 1 to Oct. 1, then I switch to a moc type that does not have white soles and will wear socks, but not white ones. White socks are for exercise shoes, white bucks, and white kid shoes, nothing else. Now Topsiders is putting colored soles on AO (authentic original) Topsiders and claiming that they are non-marking. NONSENSE! Try wearing them on a teak decked yacht; be prepared to swim. Deck shoes must have white soles. Good article.

  3. Very nice article. I currently own five pairs of Sperrys as they are perfect for Florida’s climate, they all look/feel great and hold up really well. I definitely would recommend everyone to add a pair to their collection.

  4. I’ve had Timberland and Sperry TopSiders in the past and I swear by them. One question- my current pair of Sperrys have developed a very slippery sole. They are rubber (the soles, that is) and now offer very little grip. I contacted Sperry HQ in the US and was told that the soles can’t be replaced, which I already knew. I’m wondering if you know of a method for making them grip again. I tried to use a light sandpaper on the soles in an attempt to remove a layer of rubber, but have had zero success. I even tried dragging them across gravel and concrete in an effort to remove some of the sole. No luck.
    I wore them every day while on holiday in Thailand and subjected them to some heavy usage before storing them away for a few months. When I got them out to wear them, I noticed the slippage and also that the rubber had hardened slightly.
    Time to get a new pair? That would be a shame since they’re only a year old.

    1. I have seen sprays that are supposed to make rubber stick again, but it only works for a short while. Before throwing them away, I’d use a knife and score the sole in different directions.
      For your new pair, if your Sperry shoes only last a year, why don’t you try another brand?

      1. Thanks for the reply, Sven. This particular pair lasted only a year, but I’ve had other pairs of TopSiders that have served me longer. I think I really put this pair through the ringer during a ten-day trip to Thailand where I basically wore them every day in torrential downpours, humid nights and thigh-deep in sea-water to get from a resort to the main beach (during high-tide).
        I think I’ll try the knife trick and scratch a few exxes across the sole.
        Thanks again!

  5. Hi, I have only been receiving your wonderful e-mails for a short while. During this time I have learned so much from you,ie shaving, the correct way to dress and what clothes to wear and when to wear them, Please keep up the good , work !!!!!!! Yours Faithfull .

  6. Amazing gathering of information. I especially like the Quoddy video and your brands selection (affiliate free !)

    Cheers, Nicolas

    1. Our readers come always first. That means our focus is on the quality of our suggestions, and to me it was important to list all the brands I thought were worth mentioning. Also, we were looking for the websites that offered the best price. For example Timberland on amazon was $25 less expensive than on their website, so we linked there. At the end of the day, we want our readers to get the best information, so they come back over and over again.

  7. Here’s my conundrum: I agree that boat shoes look terrible with socks, but feet perspire, causing odor to build up rapidly in shoes worn barefoot. What strategies can one employ to wear a shoe barefoot, while keeping them from becoming malodorous? I have yet to find a man’s sock that is low enough to be completely concealed while wearing a boat shoe.

    Thank you, Sven, for continuing to educate me!

    –David

    1. David, I just added a sentence to the guide above. You may want to give terry cloth inserts a try. You definitely won’t be able to see them and them should help you with your problem.

  8. Sven, I’ve never seen these inserts, before! Now I can wear my boat shoes with short pants, if I wish. THANK YOU!!

  9. You can purchase cheap insole liners at Walmart for $1 a pair. I may go through 2 or 3 sets a Summer, but my shoes I wear sockless never smell.

  10. Great & Informative article. I found a really funny article about boat shoes on the site moneycashsports.com Slightly more low-brow but nevertheless entertaining.

  11. Thanks, Sven, for another excellent article. I’m grateful to have found your site!
    I’ve tried on deck shoes in the past, including Sperrys, but find the arch support to be insufficient. Aside from using inserts, can you recommend a brand that offers good support?
    I was intersted to read your suggestion about using cornmeal to clean suede. I’ve always used a very fine grade sandpaper to clean my “dirty bucks.”I only wear them from late spring through early fall, so one or two touch-ups per season does fine and doesn’t show any excessive wear on the shoe.
    Thanks again, Sven.

  12. I also wear the Sperry Top-Sider in spring and summer, but I’ve got an alternative for autumn, which is more rugged:

  13. I would like to endorse Sebago boat shoes. About five years ago, I was looking for a good boat shoe. After I read up on the different brands, I decided to check out Sebago. I visited the Sebago Store in Georgetown, Washington D.C. While I was looking, I bumped into a gentleman who was looking for his second pair. His first pair he had on and claimed they were twelve years old. I decided to go for it and buy a pair. From the first time I wore the Sebagos, they felt fantastic. There was no break in time needed. I have been wearing them for the last five years and absolutely love them. As long as Sebago continues to live up to my expectations, I will never try another boat shoe. I have also gone through quite a few pair of boat shoe socks, trying to find something that did not show and stayed on the foot. I finally found a set of Sperry socks from a Sperry store that met my expectation. The important factor was these socks where concaved or a bit canoe shaped. I believe this shape is the key to the socks not slipping off of my heels. Good Luck Gentlemen.

  14. Sven, you missed a very good boat shoe: Rockport Ports of Call Perth, about $120. Much better arch than Sperrys, much more supportive. The leather uppers are bullet-proof. The challenge is trying to find someone who can re-sole them–a challenge I have not yet met. Any suggestions from anyone?

    1. Another great boat shoe is Quoddy. ‘If’ you ever wear out any part of the shoe, Quoddy will repair them.

  15. Good article.

    Have to say I don’t like boat shoes. I’d wear them on a boat or at the seaside, but not anywhere else. They are too clunky and not elegant enough for my taste. Kind of like baseballs caps….

  16. Once again an excellent and informative article. I’m in the market for a new pair right now and found the information especially helpful. I’m well over the half century mark and very informed yet I always learn something new when reading Gentleman’s Gazette. Thank you kindly.

    Dr William G Novak

  17. In the old days boat shoes had grommets at the insoles to let water escape. Over time this feature has disappeared. Does anyone know of a brand/model that still has grommets?

  18. I recently did buy a pair of Allen Edmonds Maritime, they are very expensive and I was counting on the good quality. I already own few oxfords and brogues from the same brand.
    Unfortunately the break in period proved to be very painful and I’m wandering if I have to give it up and replace them with another brand. Any experience guys with this shoes?

  19. Is there a difference between Sperry’s brown and white sole? It seems that the brown is much softer.

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