Deck Shoes Etiquette: How to Wear Boat Shoes with Finesse

how to wear boat shoes
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Last Updated on December 2, 2022

There is no other shoe that is as comfortable, looks as amazing with a blazer or a pair of chinos, and fits so many styles as the boat shoe.

It not only manages to be an eternal classic that never falls out of fashion. It also handles aging like a champ.

I know it might sound too good to be true, but bear with me and read on to find out all you need to know about how to wear boat shoes!

The Origin of Boat Shoes

history of boat shoes

Once upon a time, Paul A. Sperry was sailing on the Long Island Sound when he slipped on the deck and fell overboard. Deciding such an accident could be avoided with proper footwear, he went on to invent a non-slipping shoe that would guarantee it never happened again. 

The year was 1935, and what began as a lone deck shoe made of canvas or leather and a rubber sole went on to become the foundation of the Sperry company.

Later on, he added traction-enhancing grooves, copying the design on his cocker spaniel’s paws after observing how he ran down an icy hill without slipping. The process he used to cut the pattern on the natural rubber is called siping, and it continues to be used to this day.

Boat Shoes, Loafers & Moccasins

boat shoes vs loafers vs moccasins

Boat shoes have evolved a lot over the years beyond their role as sailing footwear. They have a wide range of uses that make them super versatile and very easy to combine for different casual occasions. They are sometimes confused with similar styles due to their similar aesthetic. 

Boat shoes, loafers, and moccasins are usually banded together because they are all deck shoe alternatives. However, they are each distinct styles of shoes with very different origins despite the fact that loafers are sometimes confused with a no lace boat shoe.

Loafers were originally created by a Norwegian fisherman and used in the fishing trade around 1930. The main difference between boat shoes and loafers is that they are slip-on shoes that have no ties. They also tend to have a heel. 

Moccasins were created by Native Americans from deer, buffalo, or moose skin. They consist of a piece of leather that makes up the sole and the sides and is stitched together at the top. They are easily recognized by the U shape of the toes. They can also have amazing embroidered beadwork!

Docksiders vs Topsiders

There seems to be some confusion regarding a few names under which boat shoes are known. The truth is that there is no real difference between docksiders and topsiders, both mean a casual shoe that is used on boats.

The confusion seems to have originated in the use of Topsiders by the brand Sperry for one of their classic models, whereas the term Docksiders was used much more recently by a brand called Sebago. 

The differences in design between the sturdier model by Sperry and the lighter, slightly casual take of Sebago might have created the false assumption that the terms meant different things. To complicated matters, “Sperry” is also used interchangeably as a noun to mean boat shoes, much like “Champion” is used in certain countries to mean sneakers and not the brand. 


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Socks: To Wear or Not to Wear?

which socks look good with boat shoes

There seems to be quite the debate regarding whether one should wear socks with boat shoes or not. The general rule, since boat shoes are designed to be used on boats, is that you don’t use socks with them. Or short/low-ankle socks for that matter. The logic behind it is that they could get wet and become uncomfortable. 

However, the use of boat shoes has expanded tremendously. It makes no sense to continue the rule of no socks when you are wearing boat shoes to walk around the city or in an office. Especially if it’s cold and you can feel the bitter bite of winter on your ankles.

In such cases, socks make total sense. Especially if you are wearing pants. Go for long socks so that the top won’t be visible when your pant slides up. Add some Argyles socks for extra preppiness! 

What to Wear with Boat Shoes

how to wear boat shoes

Boat shoes are one of the best shoes you can go for if you are dressing preppy. They can replace boots or sneakers and are accommodating enough for either summer or winter. They are unisex and can be worn either by women or men with little difference. Sperrys are particularly associated with a moneyed style that goes hand in hand with sailing, boating, and other nautical activities. 

With Different Types of Bottoms

Deck shoes look great with jeans, however, I would advise men to go for straight, bootcut, or classic models. Avoid skinny jeans at all costs, but even more so if you are wearing sperrys!

Cargo shorts, khakis, and tan pants look amazing with boat shoes, even more so if they are tan-colored. It’s like a match made in heaven. The most classic outfit ever. When wearing shorts, keep in mind it is best to wear your boat shoes with no socks on. It looks really tacky if the top of the socks is visible.

Joggers aren’t half as popular but they provide a bit of elegance to an otherwise very cozy and homey look. A great choice if you are lounging at home and suddenly have to go out in a hurry. Tackle a tan blazer and throw it over your sweatshirt and don some tan boat shoes to match your baggy joggers and you are set to go!

Read: Undeniable Proof that Men’s 90s Jeans are Here to Stay

With Formal Attire

Pairing a suit and a pair of sperrys is the easiest way to come up with a proper business attire without giving it much thought. It is a classic outfit that works astoundingly well in any formal or semi-formal setting.

Key tip: To keep things stylish go for leather boat shoes and match their color with the bow tie. Keep the shirt in neutral hues and if possible in a contrasting shade.

For example: A white shirt with a light blue suit and tan boat shoes with a tie that has tan, sky-blue and white colors even if they are not the exact same shade. It is best if you shop for ties with a sample of your suit cloth. When you buy a suit and have to alter the length of the pants, it is very easy to request the shop to save a little strip of cloth to accommodate later shopping. 

For Different Occasions

Boat shoes are a fashion staple. They are one of the most popular types of footwear for work, be it at an office or a shop. In truth, they are so perfect that men even go clubbing wearing boat shoes!

Of course, the fact that they look amazing in any type of trousers or jeans is one of their best selling points. However, there is also a budget equation that really weighs in. If you have a small budget for shoes, boat shoes are a great investment. They can weather a lot and will last for quite some time, they can also substitute boots, loafers, and even sneakers. Quite the catch!

Do’s and Dont’s

the dos and donts of wearing boat shoes

There seem to be a couple of misconceptions surrounding sperrys. For starters, there is the conundrum of whether they can or can’t get wet. Leather can get damaged or stained when it comes in contact with water, that much is true. However, this only happens if the leather is not properly treated and waxed. 

Boat shoes tend to either be made of canvas or leather, both properly oiled so that they are waterproof. As such it is totally safe to get them wet. Even if they were made of faux leather, they should also be completely safe to get a couple of splashes. 

Another misconception is that boat shoes are strictly summer footwear. This is not true, depending on the weather and the temperature you totally wear sperrys with socks during the cold seasons.

Also consider that boat shoes can be difficult to pull off with some types of jeans especially if they are baggy.

Best Colors for Boat Shoes

colors of boat shoes

Neutral colors are always the best investment because you can combine them with almost any color of clothing. This means that beige, white, navy, and black are the easiest to combine by far. My favorite boat shoe color is tan because it is such a classic. 

Nowadays, sperrys come in a wide variety of colors to pick and choose from. They also come in super fun combinations like turquoise and burgundy, two-toned mustard or teal and off-white.