What Men’s Hats Go Well with Your Winter Clothes?

People might not realize it, but hats are an essential part of your winter wardrobe. We bet you think that a layer of sweater or jacket is enough to keep yourself warm. If so, then you’re not getting the point. The key to staying warm is to protect your whole skin.

And by “whole,” we mean, from head to toe. Rather than just layering a sweater, vest, and jacket and leaving everything exposed from the shoulders up to your head, you should also wear something for your head, hence, the hat. But, which one?

Hats don’t just work for your overall comfort in cold temperatures and protect your face and ears from frostbite, but they can also add a lot of spice to your outfit. It could give off some handsome style to your appearance while you’re out and about. And there are a plethora of hats out there, but really, which one can you wear in winter? 

In the previous article, we’ve talked about some summer hats. Now in this article, we will talk about winter hats for men. So, are you ready to discover more winter hats besides beanies? Let’s go, then!

Types of Hats Men Can Wear During Winter

When choosing your winter hat, you can always choose between this two: a thick, practical cap for day-to-day life outside in the cold season and a far more formal, less-warming dress hat for short walks.

So, to help you find the perfect type of winter hat, we’ve listed it down for you.


Anyone from South America, or who enjoys snowboarding or other outdoor activities, will most likely recognize the name of this hat, or maybe not. And the fact that a Chullo covers the ears is one of the best features of this South American style hat.

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Chullo is traditionally made of alpaca wool with ear flaps and a cord to tie all around the chin. It is frequently designed with elaborate patterns or designs.

Watch Cap

The fit of this cap can range from tight toward the scalp to lose and piled above the head. A skullcap style is generally considered more masculine. In contrast, a softer, looser style is gender-neutral and widely worn by both males and females. And watch cap, in general, will surely keep you warm in terms of functionality.

If your watch cap is made of wool, it will most likely keep you warm. But not only that, because it also has a dressy look, which is achieved through the weave and solid dark color. See, fashion and functionality in one.

On the other hand, when your acrylic watch cap becomes dirty, you can simply toss it in the washing machine. Something you cannot do if your hat is made of wool. Also, an acrylic watch cap does a great job of wicking moisture away and retaining heat. So, it’s ideal for men who love outdoor activities during winter.


An ushanka, also known as a trapper hat or chapka, prevents your ears and chin from getting cold by placing two adjustable flaps, one on each side. It also has a string or leather tie that can be worn below the chin or on top of the hat to link them. Most have no brim, but some have an eye flap or comparatively tiny visor that helps keep the forehead heated and shades the tops of the eyes.

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There are many different styles out there, but a good ushanka or trapper hat should have a thick, furred lining and versatile ear flaps on each side of the head.

Wool Newsboy

The wool newsboy resembles a cap on top. It has the appearance of a traditional newsboy, but it is usually made of a thicker weave. Apart from the thickness, these are identical to the fall/spring designs and are ideal for anyone who wants to look fashionable while taking a quick trip outdoors. The only downside is, it will not safeguard the sides of the head.

Felt Dress Hats

There are also dress hats, such as the homburg, and dress caps with formed tops. They’ll be a little heavier because they’re made of felt. It will provide more wind protection and have a more formal appearance. However, it will not cover the ears or protect the sides of the head, but it will frequently keep the top of the head warm.

The Best Winter Hats for Men in Stores

When the weather begins to cool, it is probably the best time to start thinking about and planning your winter wardrobes outfits. But, more often than not, men may sometimes overlook one specific winter accessory until they need it the most – the winter hat. And so, to lessen your burden of finding the perfect winter hat in the market, we have listed down some of the best you can find.

Patagonia Recycled Wool Ear Flap Cap

This is a traditional cap with a winter twist. The adjustable earflaps look like trapper hats and help you warm up or cool down. At the same time, the stylistic color palette keeps things conventional.

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Canada Goose Aviator Hat

Your quest for the world’s warmest hat is over. This fur-lined trapper hat is excellent for intense cold-weather climates or whether you simply want to stand out. This has become one of the finest winter hats for bald men on the market, and it will surely provide you with the extra warmth you require.

Carhartt Whip Northfield Fleece Logo Hat

Caps are more than just a summer hat. You’ll be amazed that your favorite brands have also winterized your go-to cap for additional comfort while maintaining the same laid-back vibe you enjoy. Carhartt’s wool fleece version is a great alternative that provides a cool twist on the classic.

Mack Weldon Tech Cashmere Hat

Mack Weldon, which is known for its high-quality basics, does not disappoint with its cashmere beanie. This one is a no-brainer because it goes with everything else in your winter wardrobe.

Patagonia Nano Puff Ear Flap Carp

This quilted nylon hunting style is ideal for all who can’t tolerate the snow wadded up on their wool hat. And it a solid choice to keep you safe from whatever nature has in store for you, if you know what we mean.

The Bottom Line

When choosing for your next purchase of winter hats for men, you should always function over fashion. Sure, you will look good, but does it work well? Does it give you the warmth you need while your outside and the snow won’t stop falling?

READ ALSO: What Men’s Hats Go Well with Your Summer Clothes?

Jonathan B. Delfs

I love to write about men's lifestyle and fashion. Unique tips and inspiration for daily outfits and other occasions are what we like to give you at MensVenture.com. Do you have any notes or feedback, please write to me directly: [email protected]

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