7 Best Winter Hats To Stay Toasty And Look Fly

Shot of a handsome young man in trendy winter attire against a wooden background.

When the winter months approach, it’s time to break out your winter gear! For most people, this means big puffy coats, boots, gloves, scarves, and warm hats. However, even mild winters near the equator call for the occasional headpiece — whether for practicality or fashion purposes alone.

Investing in various winter hats can be a good idea because you can keep many different colors and styles in rotation. Additionally, there are a variety of styles and fabrics to choose from that can keep you toasty and dry for any weather condition coming your way.

For those living in those colder zones, winter hats are more than just outwear; they serve as protection from the cold climate. When the temperature drops, it is important to protect your ears and head from cold temperatures, snow, and cutting winds. According to MedExpress, “ears are comprised of mainly cartilage and do not have a lot of insulating fat, causing them to get cold faster than other body parts.” When ears lack protection, you can have ear pain, ear infections, tinnitus, and/or other illnesses.

Which winter hats are worthwhile? Read on for the seven best seasonal and (mostly) affordable hats.

How to Find the Perfect Winter Hat?

Comfort is the first thing you should look for when shopping for a winter hat. You want to make sure your hat isn’t too heavy, too hot, or itchy; these elements lead to discomfort, sweating, and/or a bad mood.

The second characteristic you should search for when looking for the best winter hat is the proper fit for your head and hairstyle. If you buy a hat that’s too small, it won’t adequately protect your head and ears. On the other hand, if you buy a hat that’s loose and bulky, it could fly off your head in windy conditions. 

The practicality of the winter hat you purchase is highly important as well. Buying a baseball cap may have you looking stylish, but will severely lack in protection and warmth if taken to a cold, snowy climate. Try searching for something with good insulation and practicality for your specific location and weather patterns.

Lastly, style should be taken into consideration when shopping for winter hats. Consider if a particular hat reflects your personality. Does it match your gloves, scarves, and other winter clothing? Does it make you feel confident in your appearance? If the answers are yes, buy that hat!

Best Winter Hats

1. Beanie

The beanie is a round brimless cap that many men love wearing during the winter months. These are also referred to as watch caps, stocking caps, skullcaps, bobble hats, and other colloquial names. Beanies are both practical and versatile hats that are typically made from natural fibers such as cotton, merino wool, or cashmere. Certain variations are made from fleece and acrylic, which sometimes feature moisture-wicking capabilities.

The original beanie has roots in 12th century Wales, where it was known as the Monmouth Cap and only outdoor workers wore them. The Monmouth Cap was named after the town it was manufactured in and fit closely to the head with a button on the top.

In the 1960s, the beanie became popular with hippies, beat poets, and other subcultures. The hat experienced a resurgence in the 1990s and has become a mainstay for a variety of people into the 2020s.

man wearing a beanie stands in from of wood wall

These six beanies are perfect for the winter months:

  • Carhartt men’s knit cuffed beanie is a clean-looking winter hat in terms of simplicity and style. It’s one size fits all and comes in a wide range of colors to suit any taste. This beanie is 100% cotton and costs $19.99.

  • Another great beanie option is the Top Level unisex beanie. This beanie is 100% acrylic, which is a high-quality material with a good amount of stretch and will keep your head warm. This winter hat comes in several colors and only costs $9.99.

  • If you’re looking for a thicker beanie for those colder months, Fantastic Zone’s beanie is perfect for you. It features a soft thermal fleece lining for optimum heat retention and premium quality acrylic that allows for some stretch in the fabric. Plus, it comes with a cozy yet stylish neck warmer for extra protection and warmth. This two-piece set only costs $14.99.

  • Another affordable yet simple beanie option is OZERO’s winter beanie. It features a thermal knit wool shell and polar fleece lining for maximum heat retention. This beanie is stylish polyester but can be useful for outdoor sports such as skiing, snowboarding, running, and more. This is a great deal at $18.99.

  • A unique but worthwhile option is Vgogfly’s slouchy beanie. The outer shell is acrylic that has a fleece lining to keep you warm and comfortable. This beanie easily conforms to the shape of your head. It comes in a variety of colors and costs $13.99.

  • The Columbia whirlybird beanie is another simple yet affordable option. This beanie is 100% acrylic and available in multiple unisex-friendly colors. It features a lightweight microfleece liner and a cashmere-like material for the outer layer, which will keep your head and ears warm. This minimalistic beanie is $20.

2. Balaclava

The balaclava is a popular winter head covering that’s basically a ski mask. It is a favorite for many outdoorsmen. Balaclavas cover the head/lower part of the face and feature a single wide slit for the eyes, the nose, and the mouth. This is perfect for extreme weather conditions and places that frequently see freezing –or below-freezing — temperatures.

The balaclava has revolutionary roots and was named after the Ukrainian port city which was the setting of the Battle of Balaclava during the Crimean War from 1853 to 1856. The knitted headgear kept British soldiers warm, and this garment eventually became a symbol of the Eastern European militia. Since then, this hat has been embraced by skiers, punk rock movements, and celebrities in the fashion world.

Black Adidas balaclava product photo Photo source: Dickssportinggoods.com

These three balaclavas are great for the winter season:

  • The Adidas Alphaskin balaclava 2 is a sleek option that will be sure to keep you warm. It has a soft fleece lining for warmth with mesh paneling for ventilation and can be worn four different ways. This balaclava costs $30.

  • The BoohooMan plain jersey balaclava is a simple yet affordable option. This all-black balaclava has no frills and will keep you warm with the polyester and spandex material. This balaclava only costs $10.

3. Trapper Hat

The trapper hat, also known as the aviator hat or the bomber hat, features ear flaps that can keep your ears, neck, and chin warm. Many trapper hats are brimless, but a select few come with a small visor for extra shade in sunny areas. You fasten the flaps under your chin or tie them together at the crown of the cap.

Trapper hats were first worn by hunters in abnormally cold climates across North America and Canada. During World War I, pilots wore aviator hats, which protected their heads and ears from icy winds in open-cockpit biplanes flying over Europe. In the early 2000s, the fashion world embraced the trapper hat for its unique look and boldness.

Man wears of trapper hat and winter jacket Photo source: Canadagoose.com

These three trapper hats are perfect for the chilly months:

  • The IYWISH’s trapper hat is a cool option with a monochrome scheme that will help you stand out among your peers. This waterproof hat gives you full coverage with ear flaps and a detachable face mask. This trapper costs $17.99.

  • Eddie Bauer’s Truckee trapper hat is another worthwhile option. It features plush faux fur ear flaps for ultra-soft warmth and faux suede drawstrings. You can purchase this hat for $50.

  • The Canada Goose aviator hat is one of the warmest trapper hats on this list, but one of the most expensive, as well. It features a coyote fur ruff visor and earflaps as well as an adjustable buckle chin strap for high-wind conditions. This aviator hat also has a water-resistant Arctic-Tech fabric for weather resistance and durability. Canada Goose has this item priced high at $325.

4. The Flat Cap 

The flat cap is a rounded hat with a small, stiff brim in the front that touts an old-school aesthetic. Also known as a golf cap, driving cap, ivy cap, and newsboy cap, they're constructed from cotton or wool tweed. No matter what you call it, this option is sure to keep your head warm during the winter.

The flat cap can be traced back to 14th century northern England, where they were referred to as a bonnet and medieval knights wore them. Thanks to an Act of Parliament, in 1571, all boys and men six years and older were forced to wear flat caps to help grow Great Britain's wool trade. The act was repealed in 1597, but these hats became synonymous with the working class.

Fast forward to the 1920s and the flat became a staple of British headwear. Flat caps have stood the test of time and have become a timeless classic across the globe.

Man wearing a flat cap hat sits in a field writing in a notebook Photo source: Sterkowski.com

These three flat caps are fantastic for the winter months:

  • The Cambridge herringbone wool newsboy cap by Jaxon Hats is a simple option that will keep you warm during the winter months. This cap is crafted of a medium-weight wool blend and features a classic grosgrain ribbon sweatband with quilted satin lining. It can be purchased for $29.95.

  • The Belfry Mennucci flat cap is a cool option with a classic look. It’s made from a blend of cashmere and virgin wool. Additionally, this hat features a plaid pattern perfect for casual and dress wear costing $89.

  • The Sterkowski Norte wool flat clap is a minimalistic option that’ll be the perfect addition to your winter hat collection. This flat cap features foldable earflaps and a sewn-down shape memory visor that slopes in the front. This flat cap costs $32.

5. Baseball Cap

The baseball cap is a close-fitting soft hat with a large visor and adjustable strap on the back. Though these are traditional accessories that many men wear year-round, they aren’t the go-to when it comes to winter hats. However, certain baseball caps are made with corduroy, tweed, or wool material, which keeps you warmer and more comfortable in cold temperatures.

In the 19th century, the earliest forms of baseball caps were made of wool with leather bills, and were only worn by baseball players. During the 20th century, baseball hats became an average piece of fashion instead of something stuck on the playing field.

The popular style people know in the 2020s became normalized in the 1940s when the crown became more vertical and the visor became firmer.

A black North Face flat cap Photo source: Thenorthface.com

These three baseball caps are ideal for the winter:

  • The Cragmont fleece ball cap is a simple yet warm option for your winter needs. It’s made from recycled polyester and earflaps can be worn down or flipped up. For $45, this hat will wick away moisture for optimal comfort.

  • The Nike unisex NSW sherpa cap is another tantalizing option for your head. It features a built-in sweatband for comfort and a faux fur shell for warmth. It comes in the color "dark driftwood" and costs $34.

  • The Merline A-Game Infinite thermal hat is another unique option on this list. This baseball cap features four-way stretch material and is water-resistant. The microfleece lining is great for heat retention, and the hat only costs $34.

6. Bucket Hats

The bucket hat is a wide hat with a downward-sloping brim that loosely resembles a bucket. This 90’s style hat comes in a diverse variety of styles, patterns, prints, and fabrics to fulfill any taste/preference. 

Also known as the fishermen’s hat, the bucket was traditionally worn by fishermen and farmers in Ireland to protect them from the rain. The British upper class embraced it and eventually, the military in World War II adopted it, thanks to its protective nature and functionality. Then, in the 1980s and 90s, the bucket experienced a huge leap in popularity due to hip-hop artists wearing them in videos and at concerts.

With celebrities such as Rihanna, Liam Gallagher, and Jason Statham wearing these functional garments, it’s no wonder they are such a hit.

Men wears a white bucket hat with a white sweater and jacket Photo source: Sentaler.com

These three bucket hats are your best bets for the winter months:

  • Himoda’s bucket hat with a fur brim is a great choice if you want to stay warm and look stylish this winter. It has a unique brim design with faux fur and complements your face shape. It’s lightweight, foldable, and comes in several different colors. This is a super affordable bucket hat at only $18.

  • The Cragmont bucket hat from The North Face is another stylish option for the winter months. It features a flash-dry headband, which wicks away moisture for optimal comfort. Plus, there’s a recycled fleece body, so you stay toasty outdoors. This black hat will only run you $35.

  • Sentaler’s Boucle Alpaca bucket hat is an understated designer option inspired by a 90s casual silhouette. The Alpaca wool is soft, durable, and eco-friendly. This bucket hat is a luxurious option that will cost you $320, but offers supreme warmth.  

7. Wool Felt Hats

The wool felt hat is an umbrella term for bowlers, fedoras, safaris, and hamburgs. If you’re looking for a classic hat with a warm fabric and a wide brim, this is the perfect winter hat for you. Plus, these are great for dressed-up occasions where you want to look dapper from head to toe 

Felt hats have existed for centuries and are known as one of the oldest textile materials around. In the 18th century, wool-felt hats were relatively cheap and theatre-goers loved wearing them. In the early 1900s, the wool felt was popular among middle and lower-class workers. In the early 1980s, the hat experienced a resurgence in popularity when Harrison Ford wore a felt hat in Raiders of the Lost Ark.

A black wool felt hat product photo Photo source: Tenthstreethats.com

The three wool felt hats are perfect for the winter season:

  • The Tenth Street Bristol felt hat is a great option if you're looking for a sleek fedora. It’s water repellant and features cotton for moisture wicking. This fashionable wool felt hat costs $62.

  • Will & Bear’s Andy Auburn wool felt hat is inspired by the outback fedora, but has a simpler aesthetic. It’s made from stiffened Australian wool and features a size-adjustable sweatband to suit any head size. This felt hat costs $149.

  • The Kenny K “Heisenberg” black wool felt pork pie hat is a stylish option that will help you make a fashion statement. It’s made from high-quality wool and features a grosgrain ribbon at the base. This felt hat can be purchased for $48.99.

Closing Thoughts

Winter hats are necessary for low temperatures — especially if you care about your health and comfort. Adequate insulation, the correct size, and style are just a few of the characteristics you should seek when shopping for the perfect winter hat.

The beanie, the balaclava, the trapper hat, and the flat clap are four amazing winter hats that will keep you warm and cozy. The final three — the baseball cap, the bucket hat, and the wool felt hat — can be worn in a variety of temperatures. When you wear any of the seven winter hats mentioned in this article, you are sure to look and feel fashionably warm.

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