Best Winter Sailing Shoes

Best Winter Sailing Shoes | Life of Sailing

Last Updated by

Daniel Wade

August 30, 2022

Keeping your feet warm and dry aboard a sailboat is essential, which is why you need a great winter shoe for sailing in the colder months.

The best shoes and boots for winter sailing are the L.L.Bean Shearling-Lined Winter Boot, the Sperry Winter Boat Shoe, the Xtratuf Waterproof Anti-Slip Deck Boot, the Shulook Waterproof Non-Slip Shoe, and the Grundens Deck Boss Foul-Weather Boot.

In this article, we’ll review five of the best winter sailing shoes and waterproof deck boots. Additionally, we’ll compare traditional natural and synthetic winter sailing shoes and cover the benefits and drawbacks of both popular categories.

We sourced shoe and boot specifications directly from their respective manufacturers to ensure accuracy.


Table of contents

Classic Vs Contemporary Sailing Shoes

What kind of winter sailing shoes are best? Classic designs (which have been used for decades, sometimes centuries) made with natural materials or modern designs made with synthetic materials? It depends, and there’s a case to be made for both.

Classic winter sailing shoes are made with materials like wool and leather. The leather is often treated with wax or an anti-water material, which sheds liquid and prevents the shoe from absorbing water. These winter shoes are exceptionally warm and long-lasting.

Modern sailing shoes are made with the latest synthetic materials. They’re extremely lightweight and affordable, and they are usually very waterproof. These shoes are ideal for sailing in the winter, as they utilize advanced materials that weren’t available decades ago.

Classic winter sailing shoes are the best choice if you want something durable that will last a long time. You’ll pay a premium, but they’ll serve you well for many years—and they’ll keep you very warm. Modern sailing shoes are best for the harshest winter environments, particularly if you’re wet all the time.

Winter Sailing Shoe Liners

The most common winter sailing shoe liners are wool, fleece, and synthetic fleece. Wool has superior properties compared to any synthetic material when wet. However, most synthetic materials are found inside waterproof shoes.

Essentially, synthetic materials will keep you warm until water finds its way in—which it is less likely to do, as the shoes are usually waterproof. Wool is the best option if water does find its way in, which it can even if you’re wearing waterproof shoes.

Best Winter Sailing Shoes

There are lots of winter sailing shoe options, and many of the best aren’t even designed specifically for sailing. The best winter sailing shoes are waterproof or water-resistant, well-made, and feature a non-slip sole that keeps traction on wet wood or fiberglass. Here are the best shoes for sailing in wet and cold conditions.

1. L.L.Bean Shearling-Lined Winter Boots

The ultimate winter sailing shoe is actually a boot, and it’s also a classic design that’s remained essentially the same for a century. The shearling-lined Bean Boot is one variety of this excellent winter shoe, and it’s been used in the harshest and wettest conditions for a long time.

Bean boots such as this one are made with waterproof leather and feature a non-slip rubber sole. This boot and its ancestors were designed in Maine, where they were used in everything from deep snow to lobster boats in harsh winter weather. This boot is lined with shearling wool for maximum wet or dry insulation.

These boots are made in the USA and feature an excellent warranty, as the build quality is excellent. Additionally, they stay warm in wet or dry conditions—as even the most waterproof boot is liable to get some water in it at some point. What makes them ideal for sailing is their non-slip bottom and waterproof exterior.

These boots are exceptionally long-lasting, and they may be the last pair of winter sailing shoes you’ll ever need. They work just as well on your boat as they do on the shore and in the snow, and their tall design makes them perfect for wet conditions. You can re-lace them with ease, and the puffy wool interior lining is comfortable with or without socks.

2. Sperry Winter Boat Shoe

Here’s another classic winter shoe that’s designed for sailing. Sperry Winter boat shoes are the best low-cut classic boat shoes for winter sailing. Sperry practically invented non-slip boat shoes and produced footwear for the United States Navy during World War II—including the shoes used in the Arctic convoys.

These shoes feature Sperry’s proprietary anti-slip sole, which has specialized cuts to prevent water from turning fiberglass and wood decks into an injury waiting to happen. Additionally, it is made with real suede-type leather that can be coated in water-resistant material.

These shoes have been produced in some form for decades, and they’ve become a style symbol in the boating community. But despite their popularity, they’re still a highly practical boat shoe for some winter conditions. They’re some of the best non-slip shoes on the market, and they’re lined for warmth.

These Sperry winter shoes are lined with genuine Australian wool, which provides warmth in both wet and dry conditions. They’re hand-sewed with tough shoe thread, which ensures a long life, and their solid leather construction is much stronger than synthetic alternatives.

3. Xtratuf Waterproof Anti-Slip Deck Boot

In the wettest conditions, a synthetic deck boot is probably the best thing you can wear on your sailboat. The Xtratuf waterproof deck boot is designed specifically for boats and provides a protective barrier to keep water out—which keeps your feet warm in cold weather.

These deck boots are made entirely of waterproof rubber material. They feature an anti-slip flat sole, which is essential on a sailboat when there’s cold wind and spray. Additionally, these boots are flexible enough to allow you to wear thick winter socks, which provide the insulation you need to stay warm.

The Xtratuf deck boots are available in four different colors, including gray, dark gray, brown, and navy blue. They’re tough due to their rubber construction, and they feature a breathable mesh interior liner for comfort. Additionally, the boots feature pull straps on both ends to help you get them on and take them off while wearing thick socks.

Slip-on boots have a few notable advantages over laced boots. When they fit, they fit well—and there are no laces to come untied and cause you to trip. These boots also feature a non-marking sole, so you can walk around your teak deck or fiberglass surfaces without scuffing or leaving damage.

4. Shulook Waterproof Non-Slip Shoes

Sometimes, a simple pair of waterproof non-slip shoes is all you need. For mild winter sailing conditions, consider the affordable Shulook Waterproof Shoes. These breathable outdoor shoes are modeled after hiking shoes, but they have great utility aboard a boat as well.

The primary defense these shoes offer against the cold is their waterproof construction. They also feature a side zipper, which makes it easy to take them off and get them on when going below into the cabin. The exterior of these shoes is suede leather, which is comfortable and easy to keep clean.

The primary benefit of these shoes is that they’re affordable and familiar. They’d work great in mild winter environments when the primary objective is to keep your feet dry. They’re a great choice for backup shoes as well, and you can keep them below in case the weather takes a wet turn, and it starts to rain.

Despite the fact that these shoes are designed for hiking, their non-slip sole actually performs quite well on boats and on the dock. Though not as effective as a true boat shoe, it will serene you better than tennis shoes on a cold sailing day.

5. Grundens Deck Boss Foul-Weather Boot

In the worst winter sailing conditions, only a set of true foul weather boots will do the job. The Grundens Deck Boss boots are an excellent choice for frigid sailing, and they’re designed specifically for use on open-cockpit boats that are exposed to the weather.

These boots feature a patented “Hercules Grip” rubber compound in the soles, which provides exceptionally good traction on the wettest and slipperiest decks. This is especially important during the winter, as falling in can be much more perilous.

Additionally, Grundens Deck Boss boots feature a long top, which allows you to tuck in your foul-weather pants above the point where water could reach them. Alternatively, you could tuck these boots into your pants instead, and the extra length provides a much more confident weather seal.

These rubber boots are both water and windproof and don’t require any special treatment or chemicals to be waterproof. Additionally, they’re designed with extra-thick material to last as long as possible. Grundens deck boots are highly-rated, and they have enough interior space for thick insulation socks.

Best Winter Sailing Shoes
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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