Quoddy Whiskey Boat Moc

Boat Shoes Explained: History, Style, How to Buy & Care Guide

This guide is all about boat shoes, including the history of boat shoes, their characteristics, where to buy them, how to break them in, how to take care of them as well as how to wear them to best effect with the rest of your wardrobe. 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 the Preppy style. 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 prefect footwear for summer months.

Sperry Top-Sider, made in Maine

Sperry Top-Sider, made in Maine


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.  The shoes available to them were just not up to the task and as one can imagine this lead to frequent accidents, not to mention hilarious and embarrassing situations.

Sperry & the Herringbone Rubber Sole

In the early 1930s, Paul Sperry, an ardent sailor and boater, 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 surfaced intrigued him. Paul figured that it had something to do with the pads of Prince’s feet. Upon closer examination he realized the cracks and grooves on Prince’s feet formed a herringbone-like pattern that gave him grip. Sperry then hit upon the idea of cutting similar patterns on the soles of the shoes he used while boating.

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

Sperry’s discover 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. Paul 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 boats’ deck, a major flaw. However, Paul quickly realized that white shoe soles don’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, still cut in a herringbone pattern. After this final modification, his shoes became quite popular among sailors and boaters but remained a niche product — they wouldn’t catch on with the general public until much later. 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 the U.S.

Characteristics of Boat Shoes

  1. Traditionally have mid- to dark-brown leather uppers. Today, uppers are available in both canvas and leather in various colors and patterns.
  2. Uppers are treated to repel water and to be stainproof.
  3. Hand-sewn and Top-stitched.
  4. Moc-toe construction.
  5. Traditionally feature a 360-degree lacing system but are also available in other styles.
  6. Usually have three or two eyelets.
  7. Laces are traditionally made of the same materials as the uppers. Now available with conventional laces.
  8. Traditionally have white, non-marking rubber soles; however they are now available in a variety of colors.
  9. Soles have a herringbone pattern carved into them.
  10. Shock-absorbing heel cup.
boat shoes in vivid colors

boat shoes in vivid colors

Where to Buy Boat Shoes

There are numerous ways to categorize boat shoes but since the originals came from the U.S., I created a list of U.S.-Made American boat shoes that have a focus on quality and heritage, as well as a category for foreign companies, designer boat shoes, etc.

US Made Boat Shoes

CompanyWhere to BuyAverage Price in $
AldenShoe Mart245
QuoddyQuoddy MTO265
Rancourt & CoRancourt Shop227
Russell Moccasin Co.Russell Moccasin Co. - Custom Only255
Eastland - Made in MaineEastland Shop295
Oak Street BootmakersOak Street Shop262
Sperry Made in MaineSperry Made in Maine300
Red Wing (not availabe in US)Redwing Germany215
New England Outerwear CompanyShop270

Other Boat Shoes

CompanyWhere to BuyAverage Price in $Made in
SperrySperry Top-Sider75
ButteroStockists360Made in Italy
Tommy HilfigerTommy Hilfiger88
Sebago & HorweenSebago & Horween150
Ronnie Fieg & SebagoRonnie Fieg & Sebago120
Ralph LaurenRalph Lauren325
Allen EdmondsAllen Edmonds115Dominican Republic

Boat Shoe Styles

Apart from the obvious, when out boating, boat shoes can be worn in a variety of ways.  In everyday wear they can replace your sneakers and loafers. 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 one school of thought, they should be worn with socks. However, most people do not wear them with socks and this contentious issue is best left to your personal preferences and comfort, since at the end of the day there is no right or wrong answer. If you are concerned that your bare feet will sweat too much but you don’t like the look of socks, you may want to try a cotton insert.

Some purists only wear either the Sperry Top-Sider (more specifically either the Original Boat Shoe in Classic Brown or the Billfish 3 – Eye in Dark Tan), or the Quoddy Men’s Boat Shoe. These styles most resemble Paul Sperry’s original design. However, there are a variety of high-quality manufacturers who offer comparable models (see table above). For those less concerned with the traditional look, boat shoes are available in an array of colors and pattern combinations which allow you to wear whatever suits your style best. These interesting videos show how Quoddy and Rancourt produce their boat shoes in Maine: http://vimeo.com/27649762 http://www.youtube.com/watch?v=WxFDqg08Ctg

When & How to Wear Boat Shoes

There are no hard and fast rules, just simple guidelines. As usual it is best to go with what you find most suitable and comfortable for yourself.

Eroll Flynn in off white boat shoes

Eroll Flynn in off white boat shoes

Obviously, boat shoes are best avoided during the winter unless you live in a hot tropical climate. They are best paired with slim, clean-lined jeans, khakis, slacks or shorts. In the summer, seersucker, madras or Nantucket reds work particularly well with boat shoes. Some people like to roll up their denims to draw the focus on the shoes — not my cup of tea but why not? Dark or white denims go very well with boat shoes especially when combined with a polo shirt or an Oxford cloth button-down shirt in solid colors or vivid stripes. To me, boat shoes are casual and I would not wear them with a suit, blazer or sport coat but that doesn’t mean you can’t wear them that way if you enjoy the look. A few years ago, most boat shoes were only available in neutral colors such as navy blue, brown, gray, beige or black. As a classic rule of thumb, boat shoes should never be lighter in color than your pants or shorts. In recent years, even classic manufacturers in Maine have begun to offer a plethora of vividly-colored shoes in ruby red, royal blue, grass green, orange, yellow… and sometimes even a combination thereof. Some boat shoes even come in three colors for a trendier look, and since all rules are made to be broken, go right ahead and wear something bright if you can pull it off. In regard to material, chrome & oil-tanned cowhide seems to be ideal but you’ll also see them in suede and patent leather. Personally, I reserve my boat shoes for casual days at the lake, a relaxed picnic or when grocery shopping in the summer but I’d never wear them for dinner parties or anything that has a hint of formality. Again, that’s just my personal preference.

Breaking in Boat Shoes

First of all, choosing the right fit is essential — boat shoes should more or less fit like slippers, meaning tight enough to hold your foot securely without limiting its flexibility. There is a rough guideline that there should be a thumbnail of extra space between the top of the big toe and the end of the shoe, but take it with a grain of salt since it really depends on your toes. When you buy a pair of new boat shoes, especially if they happen to be the traditional kind and you intend to wear them without socks, you have to break them in properly. Depending on the leather and shape of your foot you may experience painful blisters until the shoes are molded to the contours of your foot. In time they will fit perfectly. Lately, there are quite a few boat shoes on the market that are made of Chromexcel leather from Horween — it’s so soft, you will likely not experience any break-in period at all.

If your leather is stiff, good way to go about breaking in your new boat shoes is to get them wet. After all, they are meant to be worn around boats. Put on your shoes, get them wet and then let them dry wearing them. Others prefer to apply oil to their boat shoes until they are saturated. Then they wrap them in newspaper and let them dry in the shade. The oil will soften the leather which in turn will allow you to break them in without the pain. The Chromexcel leather has already undergone this softening process with natural oils, so you can definitely skip that step. Bear in mind though, everything you do to break in your new shoes is done at your own risk.

Shoe Polish

Shoe Polish

Taking Care of Boat Shoes

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

  1. 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.
  2. Avoid liquid and quick-drying polishes that contain alcohol or silicone.
  3. Keep them free of dirt, dust and salt deposits . Use a brush to do this as required.
  4. 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.
  5. 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.
  6. Dry your shoes at room temperature and avoid direct heat or sunlight to prevent them from drying out and developing cracks .
  7. Store them carefully, and use shoe trees to help retain their shape.
  8. Use a shoe horn to put them on and maintain the shape and structure of their backs.
  9. Keep a close eye on their soles and get them repaired when you see significant signs of wear and tear.
  10. One last handy tip — you can 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.
Boat Shoes in Patterns

Boat Shoes in Patterns

What are your favorite boat shoes? How do you wear boat shoes? Do you know a brand we did not mention? Let us know in the comments? This article is the result of a collaboration between Sven Raphael Schneider & Vikram Nanjappa.

20 replies
  1. Ahmed Sajeel says:

    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

  2. Jerry Finefrock says:

    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. Steven P says:

    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. teeritz says:

    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.

    • Sven Raphael Schneider says:

      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?

      • teeritz says:

        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. peter shockledge says:

    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 .

    • Sven Raphael Schneider says:

      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.

  6. David Kindred says:

    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!


  7. David Kindred says:

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

  8. Siorse O'Reily says:

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

Trackbacks & Pingbacks

  1. […] As for loafers, in my opinion they’re a bit of an odd case. It’s really difficult to find a pair that stands out from the crowd. All I can say is have a look at n.d.c (again!) to get a bit of inspiration. All you need to know and more on boat shoes at Gentleman’s Gazette. […]

  2. […] wear shorts in proper cuts and madras cloth in the summer with polo shirts, espadrilles, loafers or boat shoes, they are always reserved for very casual occasions, such as a weekend on the lake or a summer […]

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