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.

Boat Shoe Video

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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 perfect footwear for summer months.

History

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 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. 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

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

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

Other Boat Shoes

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

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.

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.

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.

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. Avoid liquid and quick-drying polishes that contain alcohol or silicone. Keep them free of dirt, dust and salt deposits . Use a brush to do this as required. 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. 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. Dry your shoes at room temperature and avoid direct heat or sunlight to prevent them from drying out and developing cracks . Store them carefully, and use shoe trees to help retain their shape. Use a shoe horn to put them on and maintain the shape and structure of their backs. Keep a close eye on their soles and get them repaired when you see significant signs of wear and tear. 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.

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.