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Best Winter Hats & Beanies for Bald Guys

Can you feel the chill in the air? It only means that winter is upon us. As the temperature drops, it can get brutal for bald heads like ours.

For those who have decided to go bald and show it off to the world like me, winter poses a challenge because it gets really cold during winter, and this is magnified when you don't have hair. When I start to feel the cool winds, it's time for me to pull out my favorite classic beanie for extra warmth.

In the past, I wore hats to hide my premature hair loss or male pattern baldness. I started going bald in my 40s, an improvement considering that my grandfather went bald in his 20s while my dad went bald and started wearing a wig in his 30s. The good news is that the social stigma attached to baldness isn't as bad as before. In fact, baldness is now seen as a sign of virility, strength, and authority.

As we look at men's winter hats from a head shaver's perspective, the goal is to protect our heads from the freezing cold weather and also to enhance our look rather than hide our baldness.

Join me as we talk about the best winter hats for bald guys and dive into why they are great for hairless scalps.


young bald man wearing a woolen beanie smiling outdoors

The Beanie is a classic winter hat that every bald man should have in his hat rack or closet. It keeps your head warm and makes you look good as well. The Classic Beanie is a staple in the UK, Norway, and Finland, where winters can be brutal.

Unsurprisingly, beanies are worn as everyday wear in countries where the temperature drops in wintertime. Beanies are also a fashion statement for bald men as they enhance your look, especially if you rock a beard. Well-known celebrities like Ashton Kutcher have worn beanies in public, which shows that the classic beanie doesn't go out of style.

It's one of my favorites during the colder months because it covers my shaved head and keeps my ears warm. Beanies come in different materials, designs, and colors, so you can easily build your collection to cover any occasion.

If you're looking for a starter hat to add to your winter collection, a beanie is a good choice.

Remember that it's best to keep your head smooth when wearing a beanie, as it can stick to your head if you have stubble.

To keep my head cleanly shaved, I can count on my Freebird FlexSeries shaver. It only takes a few minutes, and I'm done. To top it off, I also apply a post-shave moisturizer since the lower temperatures can make my scalp drier than usual.

If you're in the market for the best head shaver, you can check out our guide.

Here are our top picks for beanies:

Bart's Wilhelm Beanie - Our Top Pick

Bart's Wilhelm Beanie

Around $35

Our Content Editor Chris swears by this beanie:

"I picked this up on a trip to the UK to replace my Carhartt beanie and I couldn't be happier. I have a pretty big head and this fits without slipping off like many other "one size fits all" beanies. It keeps my head warm and looks stylish and has personality without going over the top. I love the colors."

Bart's Wilhelm Beanie comes in several stylish but subtle striped color combinations. It's made from 90% acrylic/10% polyester and features a fleece headband and a pom on top.

Fun fact: The pom on the top of some beanies was originally made so sailors wouldn't bang their heads on the ceiling of a ship when the seas got rough.

The thick, chunky knit, warm headband around the ears, and soft material will keep your ears and head warm and stylish on the coldest of winter days.

Pick it up on their website or on Amazon.

Carhartt Knit Cuffed Beanie - Best Seller

Carhartt Knit Cuffed Beanie

photo of Carhartt Knit Cuffed Beanie

Prices start at $19.49 for this best-seller by Carhartt. The Carhartt knit cuffed beanie comes in many colors, like Brite Orange, Lime, Cantaloupe, Carhartt Brown, and Winter White. This gives you endless possibilities when pairing them with your outfit. If you think that all beanies are created equal, you've never tried a Carhartt knit cuffed beanie.

They fit well even if you have a large bald head. It slides way down over your ears for extra warmth. Popular celebrities, including David Beckham, Jake Gyllenhaal, and Harry Styles, have been seen wearing these in public. If you're the type who wants to wear noticeable logos, this is perfect. People can tell if you're rocking a Carhartt.

Buy from their website or on Amazon.

The Westcoaster Arctic Circle - Best High-End Choice

photo of The Westcoaster Arctic Circle Beanie

$117 plus import charges.

If you have the budget, the Westcoaster Arctic Circle wool knit beanie from the Red Hat Factory is a keeper. Norway is known as one of the top 10 coldest countries in the world, so we trust them to make some of the best winter hats for the coldest days. When there's snow on the ground, this is the best beanie you can take out of your closet. These beanies are hand-knit for three and a half hours and are made from 100% sheep wool.

Why Wool?

  • Wool is water-resistant. They can even keep you warm when you're wet.

  • Wool is flame-resistant. Flame resistance doesn't mean wool won't burn. Synthetic fibers could ignite easily, which makes wool beanies supreme.

  • Wool is antibacterial. It contains lanolin, a natural oil found in sheep's wool. It may not protect you from infection, but it will surely keep the bad smell away.

  • Wool is a natural material. If you are allergic to synthetic materials, wool is a good alternative for you.

These amazing features come with every Red Hat Factory hat that you buy. Every handcrafted wool knit beanie you buy also comes with a Certificate of Authenticity signed with the knitter's initials.

When you place your order, you'll get:

  • Free Worldwide Shipping

  • 60 Days Money Back Guarantee

  • 10 Year Guarantee

  • 9 to 12 days shipping time

Buy from their official website.

ZOORON 1&2 Pack Beanie - Best Budget-Friendly Beanie

photo of Zooron 2 pack beanies

Prices start at $7.99 for our top pick for budget-conscious bald buddies. The Zooron cap beanies are made from polyester and cotton. They come in various colors and are One Size Fits All. They're good starter hats you can wear daily for winter activities like skating, hiking, skiing, or snowboarding. If you are thinking about winter gift ideas, you can buy a pack for you and your family.

Buy from Amazon.

Outdoor Research Cold Front Down Beanie - Best Unique Design

photo of Outdoor Research Cold Front Down Beanie

Prices start at $48.

For the more adventurous regarding style, this head-turner from Outdoor Research will surely elicit good reactions. The Cold Front Down Beanie promises to keep you warm and stylish with its 650-fill power goose-down insulation and Pertex Quantum technology. This unique beanie also features a small pocket that may come in handy as you wander out in the snow.

Other cool features include being lightweight, and wind and water-resistant. The Cold Front Down Beanie can easily be tucked into your backpack when not in use. You can choose blue, black, and gray colors to match your winter wardrobe.

Buy from their website.

GUCCI Wool Knit Hat With Web Stripe - Splurge

photo of Gucci Wool Knit Hat With Web Stripe


An expensive Italian-made beanie by Gucci? Why not? Who wouldn't recognize the green and red Gucci colors and logo? The Gucci Wool Knit Hat features camel knit wool and a stylish pom-pom design. Keep in mind that these beanies should be dry-cleaned only. If you need to iron to remove creases, use low heat. You wouldn't want to ruin a $500 beanie.

Buy from their website.

The Aviator Hat

bald man wearing an aviator hat outdoors in winter with his family in the background

The Aviator hat was born when airplane cockpits were completely open. Pilots needed to keep their heads and eyes warm during flights, and the Aviator hat provided just what they needed. It had a low brim and long ear flaps, providing excellent protection in severe weather conditions.

Aviator winter hats for men were usually made from fleece lining or faux fur, which are good insulators against the cold weather.

I feel nostalgic while writing about aviator hats for men since my great-grandfather and grandfather were both pilots. In fact, The Fernando Air Base in Lipa, Batangas, was named after my great-grandfather, Lt. Col. Basilio Fernando, the "Father of Philippine Aviation." My grandfather, on the other hand, Capt. Eduardo Fernando Sr. was the first Filipino to break the sound barrier.

Fernando Air Base Welcome Marker at Lipa City Batangas

When I was younger, I also dreamed about becoming a pilot one day, but I didn't meet the height requirement! It doesn't matter. I am happy to write valuable information for fellow bald people out there.

I would have encouraged them to ditch their wigs and start shaving if they were all alive today. They would have loved using our Freebird FlexSeries shaver and our complete line of shave and scalp care products.

I can imagine them with their shaved heads, wearing beanies and aviator hats during the cold season while we talk about how to care for our bald heads.

Trapper hats are similar to aviator hats in design but usually have a super soft fur lining for extra comfort and warmth during the most extreme of cold weather.

Zavelio Unisex Shearling Sheepskin Leather Aviator Hat

photo of Zavelio Shearling Sheepskin Leather Aviator Hat

Prepare to spend $59.99 and upwards for this 100% genuine sheepskin Aviator Hat from Zavelio. The Zavelio Aviator hat is a classic winter hat that comes in different sizes and colors. It's one of the best winter hats you can buy and is a great choice for those who love outdoor activities like snowboarding, hiking, trekking, camping, hunting, and skiing.

Zavelio makes handmade Aviator Hats that are lightweight, water-repellent, and durable due to their leather construction. Tie straps are also a good feature with this winter hat since you can secure your earflaps either up or down. With the Zavelio, you are sure to keep your head, ears, forehead, and neck warm.

Buy from their website or on Amazon.

And Wander Black Primaloft Aviator Hat

photo of And Wander Black Primaloft Aviator Hat

Prices start at $150.

How about trying one of the best winter hats from a Japanese fashion house for a change? And Wander is a brand that's been with us for more than a decade. The design duo of Keita Ikeuchi and Mihoko Mori have come up with an aviator hat for winter. This winter hat is a good choice if you are going for the minimalist look.

The Primaloft Aviator hat is made from water-repellant nylon Pertex and lined with faux fur and taffeta for ultimate winter protection. The ear flaps are lined with fleece to keep you warmer even in harsh winter conditions.

Buy from their website.

Eddie Bauer Superior Down Trapper Hat

photo of Eddie Bauer Superior Down Trapper Hat


The Superior Down Trapper Hat by Eddie Bauer is a good winter hat to keep you warm and comfortable all winter long. If you love winter activities, you can go out in style by wearing your trapper hat matched with your casual wear.

The Superior Down Trapper Hat features a water-resistant acrylic polyester shell with down insulation for extra warmth. For added comfort, a faux fabric lining is included.

Buy from their website or on Amazon.

Baseball Cap

photo of a bald guy wearing a baseball cap in winter with his wife and baby girl

Who doesn't own a baseball cap? You get a hat that's timeless when it comes to style. You can also pair them with any outfit with ease. This is my hat of choice, and I like to wear them all year round.

It's good to know that baseball caps can keep you warm during winter. It's because of their snug fit and unique shape.

Carhartt Defender Canvas Earflap Cap

photo of carhartt defender canvas earflap cap

Prices start at $29.99.

Another warm hat from Carhartt that is worth adding to your hat rack. It features an insulated, water-repellant material with sherpa-lined ear flaps.

Going outdoors with light rain and snow? The Rain Defender can protect you from both. You'll surely appreciate being dry in light rain. It's also easy to wear with ear flaps down during colder days and tuck them up when the mercury rises a bit.

The famous Carhartt label is sewn in front of the cap, which is great for your personal style.

Buy from their website or on Amazon.

LL Bean Wool Blend Ball Cap

photo of LL Bean Wool Blend Ball Cap


If you love to wear your classic baseball cap during winter, it's a good idea to pick wool baseball caps for lightweight warmth. The LL Bean Wool Blend Ball Cap easily adjusts to your head and has a wool polyester rayon blend crown that fights the cold and does moisture-wicking.

Buy from their website.

The Final Word

bald men wearing beanies having fun at a Christmas party

Who says that we bald guys can't fight the cold and be stylish at the same time? Yes, we may feel colder than the rest during winter since hair traps heat and protects from the cool breeze.

We may also be more prone to cracked, dry, and damaged skin during winter. But with the right winter hat, you can stay warm and protected. Aside from winter hats, I always use a post-shave regimen to prevent dryness during the cold season.

After reading our recommendations for men's winter hats, you can now start adding them to your collection. You can never go wrong with a cap beanie to start off, then move on to an aviator or trapper hat to further differentiate your style.

It's time to embrace the winter season and knock off those bald-head blues.

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