Andrew Pace
Boat shoes have gone in and out of fashion over the years, but they remain a classic casual shoe trend in the menswear world. Originally designed for sailors to wear on slippery boat decks, they are now commonly worn by boaters and non-boaters alike, both for functional and aesthetic reasons.
So, should guys wear boat shoes? Well, that's up to them. But if they do, there are a few things to keep in mind. Firstly, boat shoes are casual footwear, so they're best paired with smarter casual clothes like polo shirts, button-down shirts, chinos, jeans, or shorts. They're also typically a spring and summer style, so it's best to save them for warmer weather. And finally, while it's generally recommended to avoid visible socks with boat shoes, no-show socks can be a comfortable and practical option.
| Characteristics | Values |
|---|---|
| Best worn with | Jeans, chinos, shorts, denim, colourful trousers, suits, cuffed jeans, tailored shorts, tapered or straight-leg jeans or khakis |
| Not to be worn with | Suits, formal occasions, in the winter, visible socks |
| Best worn to | The beach, when travelling, the office (business casual), on a date, casual bars |
| Not to be worn to | Weddings or other black-tie events |
| Best worn in | Warmer weather |
| Not to be worn in | Winter |
| To be worn with | No-show socks, loafers |
| Not to be worn with | Socks (according to some sources) |
| Best colour | Brown, navy, neutral leather |
| Worst colour | Red, green |
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What You'll Learn
Boat shoes: a brief history
Boat shoes, also known as deck shoes or topsiders, have a long and interesting history, shaped by functionality, fashion, and practicality. Here is a brief history of the boat shoe:
The Early Days
Boat shoes were first created in the early 20th century, specifically for sailors. The story of the boat shoe is often attributed to Paul A. Sperry, an American sailor and inventor, and former Navy sailor. In the 1930s, Sperry noticed that his dog had excellent traction on slippery surfaces due to the grooves on its paws. Inspired by this, he set out to create a non-slip shoe for sailors navigating slippery boat decks.
The Birth of the Boat Shoe
Sperry developed the first boat shoe by carving grooves into the rubber sole of a standard shoe using a penknife. This innovative design provided better traction on wet surfaces, reducing the risk of slips and falls. The original boat shoe featured a leather upper with laces and a rubber sole with a distinctive siping pattern for improved grip.
Gaining Popularity
During World War II, the U.S. Navy adopted boat shoes for their practicality and functionality. Sailors and naval officers appreciated the slip-resistant soles and comfortable design, making them ideal for long hours on deck. After the war, boat shoes transitioned from function to fashion, gaining popularity among the sailing set in the Northeast and Great Lakes.
The Rise of the "Preppy" Style
In the 1960s, boat shoes experienced a surge in popularity, becoming a staple of preppy fashion. Icons of early 60s style, such as John F. Kennedy Jr. and Jacqueline Kennedy Onassis, were often photographed wearing boat shoes, further contributing to their rise in popularity.
A Timeless Classic
Over the years, boat shoes have remained a timeless classic, transcending trends and maintaining their appeal across generations. While they are still favoured by sailors and boating enthusiasts for their practicality, they have also become a versatile wardrobe staple. Today, boat shoes are available in various materials, colours, and designs, catering to different tastes and preferences.
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When to wear boat shoes
Boat shoes are a versatile shoe that can be worn in a variety of settings. Here are some tips on when to wear boat shoes:
At the Beach or on a Boat
As the name suggests, boat shoes were originally designed for maritime activities, so they are perfect for a day at the beach or a trip on a boat. Their non-slip rubber soles provide excellent traction on wet surfaces, making them a functional and stylish choice for these environments.
When Travelling
Boat shoes are comfortable and easy to take on and off, making them ideal footwear for travelling. They are also versatile and can be dressed up or down, so you can explore new places in style and comfort.
In a Business Casual Environment
Boat shoes can be a great choice for the office, especially if you work in a business casual setting. They add a touch of style to your outfit without being too formal. However, if your workplace is more formal, you may want to opt for a different type of shoe.
On a Casual Date
Boat shoes can be a great conversation starter and can show off your personality. They are perfect for a casual date, adding a touch of style while still being laid-back and relaxed.
In Warmer Weather
Boat shoes are typically associated with spring and summer styles. Their low cut and softer, thinner leather make them most suitable for warmer months. They pair well with lightweight pants and shorts, and their exposed design keeps your feet cool and comfortable.
With the Right Outfit
Boat shoes are casual footwear and can be dressed up or down. They look best with nicer casual clothes, such as polo shirts, button-down shirts, or henley shirts. For bottoms, pair them with tailored shorts or well-fitted jeans or chinos. Cuffing your jeans can also complement the boat shoe look. Avoid wearing boat shoes with suits or extremely formal attire, as they are too casual for black-tie events.
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What to wear boat shoes with
Boat shoes are a great choice for a smart-casual look. They are a preppy staple and are best worn with chinos and polo shirts or a button-down shirt, short-sleeve henley, or guayabera. You can even wear them with a blazer, but only if you dress down the rest of your outfit.
Boat shoes are incredibly versatile and can be worn with jeans, shorts, or trousers. If you're wearing jeans, try cuffing the hems for an effortless, nautical look. When wearing shorts, opt for a plainer, more tailored pair to balance out the attention-grabbing boat shoe. For trousers, a cropped or shorter length is best.
When it comes to colour, boat shoes typically come in a variety of colours, but it's best to stick to darker neutrals like brown or navy. These colours will complement your outfit without being too flashy.
It's important to note that boat shoes are designed for warmer weather and should be avoided in winter. They are also not suitable for formal occasions or black-tie affairs. Instead, they are perfect for the beach, travel, casual Fridays at the office, and dates.
Lastly, while boat shoes can be worn with socks, it's generally recommended to go sockless or use no-show socks. Visible socks can ruin the look, although this rule can be bent if you're experimenting with a new-wave take on '80s Ivy League prep.
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$12.99
Socks or no socks?
Boat shoes are a timeless classic in menswear and can be worn in a variety of settings, from the beach to the office. But what about socks? Should you go sockless or not?
The traditional way of wearing boat shoes is without socks, and most people prefer to keep their ankles bare for the classic maritime look. This is also the most practical option when actually going out on the water, as it allows your feet to breathe and stay cool. However, there are some drawbacks to this approach. Not wearing socks can be uncomfortable, especially if your shoes are new and need to be broken in, and it can also lead to foot odour and even foot fungus issues such as athlete's foot.
So, if you want to wear socks with your boat shoes, what type should you choose? The key is to pick the right kind of sock to maintain the casual, preppy aesthetic associated with boat shoes. No-show socks are a popular option as they give the appearance of being sockless while still providing some comfort and protection for your feet. They are designed to be invisible when worn with boat shoes, so you can achieve the sockless look without the potential drawbacks. If you don't like the idea of no-show socks, you can also opt for dress socks, which provide a slightly more formal look while still maintaining the relaxed and casual vibe of boat shoes. Just make sure to avoid athletic socks, which are too casual and should be reserved for athletic shoes.
In terms of colour, it's best to match the colour of your socks to the colour of your shoes, especially if you're wearing no-show socks that might be visible from certain angles. If you're going for a more formal look, such as with long pants and a blazer, calf-length socks are acceptable, but avoid this combination if you're going for a shorter length trouser or a more casual outfit.
Ultimately, whether you choose to wear socks or go sockless with your boat shoes is a matter of personal preference. Both options can be stylish and practical, so choose the one that makes you feel most comfortable and confident.
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How to break in your boat shoes
Breaking in boat shoes can take anywhere from a week to a month, depending on how much you wear them. Here are some tips to help speed up the process and ensure a comfortable fit:
- When you first take the shoes out of the box, feel around for any hard spots in the leather and massage them out. Check inside the shoe as well for any pointy thread ends that could be an irritant and snip them off if necessary.
- Start wearing the shoes slowly and in short intervals—first around the house, and then for short errands. If they create a hotspot or blister, cover it with a band-aid and continue wearing them.
- To accelerate the process, some recommend soaking the shoes in water. Fill a bathtub or a large bucket with about 6 inches (15 cm) of warm water and add a tablespoon of sea salt for every 1⁄4 gallon (0.95 L) of water to achieve an ocean-like salinity. Put on your shoes without socks and lace them up tight. Stand in the water until the shoes are fully saturated, rocking forward and backward to stretch the material. Towel-dry the excess water, and then wear the shoes until they're dry. The leather will first expand and then shrink to mould to the shape of your feet.
- Leather shoes, in particular, will benefit from being worn a lot when they are new and the leather is most pliable. Leather also tends to dry out over time, so consider treating them with a leather conditioner to add moisture and keep them in top shape.
- Make sure you're wearing the right size. Your feet should be comfortable with room to wiggle your toes, and the shoes should be snug enough not to fall off. Too-tight or too-loose shoes cannot be broken in for a good fit.
- Whether or not you wear socks during the breaking-in process will also affect how the shoes mould to your feet. Socks will make the shoes feel tighter and may stretch the leather, so if you break in the shoes wearing socks, they may feel loose when you wear them without socks.
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