Ready for the Freeze? 14 Winter Hats for Men To Wear in 2021

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Image Courtesy of LL Bean
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Contrary to what the kid from Jerry Maguire says, the average human head weighs more than 8 pounds (try telling that to his adorable face, though). We also don’t lose half of our body heat through our heads — studies show that amount lost is proportional to the amount of skin showing. There’s a weird amount of myths about the human head, but one thing is certain — a comfortable winter hat will help keep you warm in cold weather, regardless of how much your noggin weighs.

Of course, the best winter hat for men isn’t just one that’s insulating and comfortable, but also one that’s stylish. After all, a hat is one of the first things someone will see when they look at your face.

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The most universally flattering and versatile winter hat for men is a beanie. Whether it’s acrylic, wool or cotton, the right beanie will provide plenty of warmth and a dash of style. That said, a beanie isn’t the only option. A bucket hat isn’t as insulating, but a water-resistant one can help keep you dry on a wet winter day. And if it’s particularly frigid, an ushanka (a Russian hat with a fur lining and ear flaps) is sure to keep you toasty. These are some of the best winter hats for men to buy.


1. Carhartt Men’s Knit Cuffed Beanie


The Carhartt beanie is a classic for a reason — it’s affordable, warm, stylish and available in three million colors, give or take. It’s made from acrylic and is meant to be hand washed. The cuff can be adjusted as needed for a more comfortable fit. We named this the best winter hat of 2020, and we may just do so again this year.

winter hats for men Image Courtesy of Amazon

Carhartt Beanie


2. Amazon Essentials Knit Beanies – 2 Pack


Amazon Essentials is a great go-to clothing line for everyday basics. This 2-pack contains a gray and black knit beanie that will keep your head and ears warm on those chilly winter days on the horizon. The colors will go with just about everything, and the price is pretty hard to beat.

Amazon Essentials Knit Beanies Courtesy of Amazon

Amazon Essentials Knit Beanie


3. Drake’s Lambswool Hat


Drake’s makes some of the finest men’s accessories, and they’re known worldwide for their ties. This beanie is made in Scotland from 100% lambswool, and it has a ribbed texture that adds extra visual flair. The dark green color is great for autumnal and winter tones. Available via Todd Snyder, it will go great with the designer’s new L.L.Bean collaboration.

winter hats for men Image Courtesy of Todd Snyder

Drake's Beanie


4. Madewell Wool Five-Panel Baseball Cap


If it’s not cold enough for a beanie, but you still want a warm hat that’ll tame your bedhead, consider getting a wool baseball cap. It’ll offer a little warmth while also complementing the look of wool jackets and sweaters.

winter hats for men Image Courtesy of Madewell

Madewell Wool Cap


5. Patagonia Fisherman’s Beanie


Patagonia’s beanie is made from a recycled polyester fabric, making it a great option if you find wool and acrylic itchy. The ribbed texture makes it stretchy, while also adding appealing visual texture. It comes in a range of colors and has a small Patagonia logo on the cuff. What can we say — we just really love this hat.

winter hats for men Image Courtesy of Patagonia

Patagonia Fisherman's Beanie


6. A Kind of Guise Khoni Trapper Hat


Trapper hats and ushankas are unbeatable when it comes to warmth, but they can sometimes leave you looking like you stepped out of a Jack London novel. This trapper hat from A Kind of Guise comes in muted navy with a tonal shearling lining. The hat is made from a blend of wool and cotton, with a polyester faux-shearling.

winter hats for men Image Courtesy of Mr Porter

A Kind of Guise Trapper Hat


7. LL Bean Men’s Pistil Tinh Beanie


Waffles aren’t just for eating — the waffle texture of this beanie allows it to easily stretch, while also providing insulation. It has a classic cuffed design and is available in several muted colors. It’s made from acrylic.

winter hats for men Image Courtesy of LL Bean

LL Bean Beanie


8. Rains Bucket Hat


Sometimes winter is cold, and other times it’s cold and wet. This Rains bucket isn’t as insulating as a wool beanie, but it’ll keep you dry, which is important for staying warm. It comes in a range of colors and features a subtle Rains tab logo.

winter hats for men Image Courtesy of Verishop

Rains Bucket Hat


9. Filson Watch Cap Beanie


Filson is known for its legendary bags and outdoor clothing, and this watch cap brings a sense of the outdoors to your everyday routine, even if that just entails catching the bus to work. The orange “flame” color is a great eye-catching option. This beanie is made from American-sourced wool.

winter hats for men Image Courtesy of Filson

Filson Beanie


10. Goodthreads Men’s Sherpa Trapper Hat


We like this Goodthreads take on the classic trapper hat. Instead of fur (or faux fur, more often) on the inner lining, these winter hats feature a sherpa-style lining. We also love the stylish check pattern, which makes this trapper hat stand apart from other winter hats for men.

sherpa trapper hat Courtesy of Amazon

Goodthreads Men's Sherpa Trapper Hat


11. Gap Organic Cotton Ribbed Beanie


Synthetics and wool can be itchy, which is why cotton is king when it comes to softness. This beanie from Gap is affordable and made from a blend of organic cotton and acrylic. Best of all, it comes in a ton of different colors. Stock up and stay warm all winter long.

winter hats for men gap Image Courtesy of Gap

Gap Beanie


12. LL Bean Adults’ Katahdin Pom Hat


If you’re not afraid of making a style statement, go with this pom hat from LL Bean. It has a mountain-inspired print on the beanie with a pronounced LL Bean logo on the cuff. If you wear it in the city, it’s as good as an “I’d Rather Be Camping” bumper sticker.

winter hats for men Image Courtesy of LL Bean

LL Bean Beanie


13. Target Goodfellow & Co Men’s Speckled Knit Beanie


Need an item of clothing quickly and don’t have much to spend? Target has you covered. This beanie has a stylish speckled pattern and a ribbed texture. It’s made from a blend of acrylic and polyester, and the internal lining keeps you comfortable and warm.

winter hats for men Image Courtesy of Target

Target Beanie


14. Amazon Essentials Plaid Trapper Hat


Not every man can pull off a trapper hat, but if these winter hats suit your sense of style, then more power to you! This plaid trapper hat will keep you warm and cozy all winter long. The ears, inner surface and forehead are lined with faux fur for comfort. This men’s winter has is also available in blue or black.

amazon trapper hat Courtesy of Amazon

Amazon Plaid Trapper Hat



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