Best Winter Sailing Hats

Best Winter Sailing Hats | Life of Sailing

Last Updated by

Daniel Wade

August 30, 2022

Your body loses lots of heat through your head, so a well-made and warm sailing hat is essential for winter weather.

The best hats for winter sailing are the Smartwool Merino Wool Cozy Cabin Hat, the RockBros Cold Weather Thermal Balaclava, the Home Prefer Winter Skull Cap, the Vgogfly Trapper Windproof Winter Hat, and the Otter Waterproof and Windproof Winter Hat.

In this article, we’ll review five of the best hats for cold and wet winter sailing. Additionally, we’ll compare common winter hat materials, including wool, fleece, and synthetic, and we’ll cover the qualities that make the best winter sailing hats.

We sourced product specifications directly from each hat’s distributor to ensure accuracy.


Table of contents

Wool Sailing Hats

Wool hats have been used on boats and ships for centuries, especially during the wintertime. Wool, when un-encapsulated, is a remarkably good sea hat as it retains heat even when it's wet. Additionally, wool is naturally fire retardant (compared to synthetics) and very difficult to tear.

Wool hats alone are sufficient in some climates, especially when kept dry. Wool sailing hats are also a great choice to wear underneath a waterproof synthetic hat, which will keep the wool dry and working at 100% insulation.

Synthetic Sailing Hats

In warmer climates, people often prefer synthetic sailing hats that are lined with some sort of insulation, such as 3M Thinsulate. Synthetic sailing hats have a few notable advantages, namely that they’re waterproof and bead off the water instead of soaking it in.

Truly waterproof synthetic hats are a great option for winter, but they have some notable limitations. If the hat is lined with an insulating material, which most winter sailing hats should be, the inside is not protected from soaking up water.

Synthetic insulation doesn’t have the same properties as wool, and it can quickly become a heatsink on your head if water gets inside. It’ll also take quite a long time to dry. However, synthetic hats break wind much more effectively than any natural materials.

The best synthetic sailing hats for winter should be protected from water ingress. These higher-quality winter sailing hats are designed to keep you warm regardless of the weather conditions, and they’re comparable to wool in terms of wet-weather usefulness.

Fleece-Lined Hats

Fleece-lined hats are a popular choice for winter sailing, as they’re lightweight, warm, and comfortable. These hats are sometimes pure fleece but often covered in a water-repellent or waterproof synthetic material.

Fleece hats are usually the most affordable winter sailing hats. Fleece itself is also available as synthetic material, which has similar properties to real fleece. However, genuine fleece is usually superior and long-wearing compared to artificial materials.

Best Sailing Hats for Winter

The best winter sailing hats are often just winter hats with superior weather-resistant qualities. However, some are designed specifically for sailing. Here are five of the best winter hats for sailing.

1. Smartwool Merino Wool Cozy Cabin Hat

Sometimes, an old-fashioned wool beanie hat is the best choice for long hours in cool weather. Wool insulates effectively, stays warm when wet, and lasts longer than you’ll probably ever keep it. The Smartwool Unisex Cozy Cabin hat is one of the best merino wool hats on the market, especially for winter sailing.

This stretchy wool hat is woven finely and features high-quality insulating material. The benefits of the fine weave (when compared to knit hats) are numerous, as the hat insulates better and is less affected by water. Additionally, this hat has excellent elasticity, which ensures a comfortable and snug fit.

The Smartwool Cozy Cabin hat is made in the USA, and it’s machine washable. Smartwool has a reputation for producing high-quality products, and this hat is no exception. These wool hats have special qualities, including odor-reducing properties and a proprietary blend for superior insulation when compared to synthetic hats.

The primary benefit of this wool hat over others is that Smartwool’s blend is easier to keep clean and more comfortable than traditional wool hats, and it has superior insulating properties compared to fleece or synthetic hats. It’s designed for outdoor use and retains heat when wet with saltwater or freshwater. It’s ideal for all except the coldest and wettest sailing environments.

2. RockBros Cold Weather Thermal Balaclava

Sometimes, you need a hat to cover more than just your head. And in especially cold conditions, a thermal balaclava is the way to go. The RockBros Cold Weather Balaclava is a fleece scarf, mask, and hat that keeps you warm when the cold wind blows. And on a sailboat, a windproof head insulator can be absolutely vital.

Much of your body’s heat escapes through your head. This can be a major problem, especially when it’s cold and windy. Additionally, UV burns during the winter can be bad—especially on a white fiberglass sailboat. Being surrounded by water reflects the sun, which can burn you and cause skin damage even when it’s cold out.

The RockBros balaclava is designed to protect you from cold, wind, and the sun’s damaging rays. Additionally, it serves as a face mask, which keeps your cheeks warm and reduces dust inhalation in the event that you need to make repairs. And thanks to its real fleece lining, the RockBros Balaclava is one of the warmest on the market.

The RockBros Balaclava is a great winter sailing accessory for windy days, though it doesn’t offer the most protection from water. This wind-breaking hat will serve you well in the Pacific Northwest or on the East Coast, as long as you’re not getting completely drenched. It is sufficient for wet weather when combined with a waterproof sailing suit.

3. Home Prefer Winter Skull Cap

The Home Prefer Winter Skull Cap is a warm fleece hat with special flaps to cover your ears. This hat can be worn alone or under the hood of a waterproof sailing suit, and it has a sun brim to protect your face from UV burns. A hat like this offers excellent warmth and preserves visibility, which is essential on a sailboat.

The Home Prefer Winter cap is made of real fleece, which is lightweight and provides great insulation in cold weather. It’s not windproof, but the material is thick enough to dampen most wind conditions encountered on sailing days. Additionally, it’s available in red, fluorescent orange, olive drab green, navy blue, gray, dark gray, and black.

The Home Prefer cap is available in multiple sizes, so you’ll have to measure your head before purchasing one. It’s highly affordable, which makes it a great accessory to toss in your sailing bag in case the weather gets chilly. It’s designed for cold weather and will work on most colder days except the most frigid.

The headband absorbs sweat, which is a major plus if you’re working and wearing thick clothing. Plus, it’s easy to clean and features an elastic tightening strap for days when the wind is strong, and you need an extra-snug fit. The Home Prefer winter cap is ideal for sailing in 30 to 50-degree weather.

4. Vgogfly Trapper Windproof Winter Hat

Here’s a variant of a classic hat design that’s made solely for utility on ultra-cold days. The Vgogfly Trapper winter hat is based on the iconic Russian Ushanka, which was worn by military and navy personnel in the Arctic and Siberia. This version has a synthetic outer layer and thick cashmere wool on the inside.

This Ushanka-style hat has large insulated flaps for the ears and chin and a strap to connect them. Additionally, it has a synthetic snap face cover that leaves a slit for your eyes—and offers maximum facial protection from harsh weather. This is a true cold-weather hat that will keep you warm in frigid conditions.

These hats are designed to protect you from sub-zero temperatures, reducing the risk of frostbite on your nose and other unpleasant effects of the cold. Additionally, it protects you from harsh winter UV rays, which are an often-overlooked risk of winter sailing. It provides some level of water resistance as well, which will protect you from the icy spray.

This hat can be worn with or without winter sailing clothes. It’s also available in tan, black, blue, gray, and red—so you can find one that matches the rest of your waterproof sailing gear. This hat is surprisingly affordable given the protection it offers, and it’s rated highly by hunters, anglers, hikers, and sailors.

5. Otter Waterproof and Windproof Winter Hat

The ultimate winter sailing is one that’s waterproof, windproof, and insulating. Here’s a synthetic winter hat that’s made with breathable material for the best comfort and a high-quality winter lining. The Otter winter hat is available in seven colors and made to last for years.

Otter chose nylon and a Lycra closure for comfort and durability. It uses acrylic yarn that, by design, doesn’t absorb water. Unlike wool, which retains warmth when soaked due to its natural properties, acrylic retains warmth because it repels water entirely.

On the inside, the Otter hat features a polyester fleece lining that retains heat and increases comfort. Combined with its soft waterproof outer layer, this hat has superior insulating qualities even in the wettest sailing conditions. These properties make it ideal for winter sailing in heavy weather, especially when combined with winter sailing clothes.

The Otter hat is 100% waterproof, which is unusual for a soft hat that feels like a standard wool beanie. It’s not wool, and as a result, it’s a lot more affordable than many natural hats with similar properties. The hat also features a microporous membrane, which is too small for water to soak into but large enough to allow your head to breathe.

Best Winter Sailing Hats
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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