18 Best Winter Hats for Men 2021

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As the temperature begins to drop, it’s time we start looking ahead and planning our winter wardrobes. More often than not though, we tend to overlook a certain cold-weather accessory until we need it most: the winter hat. And while it’s hard to go wrong with a classic beanie, there are a variety of winter hats that we can have in our arsenal to keep us both looking dapper and feeling warm.

Below, we break down the different types of hats and the 20 best winter hats for men available now.

Read more: Winter Style Trends for Men

Trapper Hats

This style of hat comes with ear-flaps that can either be tied up to the crown of the cap or fastened at the chin to protect and warm the ears, neck, and chin from the cold. These styles usually come lined with fur or shearling for added warmth.

Beanies

The classic beanie is a head-hugging brimless cap made from triangular panels of material joined at the top of the crown.

Driving Caps

This winter hat style—also called newsboy caps or flat caps—is a rounded cap with a small stiff brim in front originating from the United Kingdom. Think Peaky Blinders, but made for the modern man.

Ranger Hats

Inspired by the American West, these outdoorsmen hats are part cowboy, part park ranger, and come with a full wide brim and tall crown.

Balaclavas

For the extreme outdoors, balaclavas are essentially a fancy name for a ski mask, usually with a single wide slit for the eyes.

Baseball Caps
While not initially thought of as a winter hat option, designers are rendering these classic styles in textural winter fabrics—think wool, tweed, and corduroy—that allow them to provide more warmth and comfort in the cold.

Bucket Hats
This quintessential ’90s style features a wide, downward-sloping brim that sits directly on the crown and completely covers the head.

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Best Beanie

Mack Weldon Tech Cashmere Hat

Known for their high-quality basics, Mack Weldon’s cashmere beanie does not disappoint. Easily paired with almost all of your winter outfits, this one is a total no-brainer.

Huckberry Beanie

The classic beanie comes in many shapes and sizes, but this extra-thick ribbed version elevates the style to the next level. Thanks to an extra-long length, the wearer can roll this version up for a more fitted appearance or wear it down for a cool slouch effect in the back

Read more: Best Winter Jackets for Men

Patagonia Recycled Wool Ear Flap Cap

A classic cap with a winter twist. The adjustable earflaps resemble those of a trapper hat to help you warm up or cool down while a tonal color scheme keeps things modern. 

Read more: Best Black Friday Clothing Sales for Men

Best Cap

Herschel Whaler Cap

Caps aren’t just a summer hat. Your favorite brands winterized your go-to hat for added warmth with the same laid-back vibe you love. This wool version from Hershel is a great option that offers a cool contrast in texture and color.

Brixton Hooligan III Driving Cap

For those gentlemen who feel too confined by the beanie, we suggest a classic newsboy hat silhouette. This herringbone version has a vintage air to it that still feels fresh for today.

Carhartt Knit Cuffed Beanie

Carhartt has created a cult classic that continues growing in popularity year after year. Offered in almost any color you can imagine, this affordable winter hat simply never goes out of style. 

Stretson The Bozeman Hat

While this may not immediately register as a winter hat, we can assure you that it’s one of the warmest men’s hat styles out there. Rendered in wool felt, this outdoorsman hat is the perfect transitional wardrobe staple: shading you from the elements while keeping you warm.

Canada Goose Aviator Hat

Your search for the warmest hat in the world is over. This fur-lined trapper hat is ideal for extreme cold-weather climates or if you just want to make a statement. This is also one of the best winter hats for bald guys on the market, guaranteed to provide the extra warmth you need. Plus, this also makes for a great gift for guys.

Amazon Essentials Men’s 2-Pack Knit Beanie Hat

These knit beanies are an ideal shape with soft-yet-durable fabric for both fall and winter. We have our eye on this brightly colored orange and charcoal set, because two is simply better than one. 

Everest Designs Dapper Don Beanie

Soft, double-strand, sustainable New Zealand wool provides the foundation to this high-quality hat that is completely hand-made, while a color-blocked cuff adds a little something unexpected. 

Adidas Alphaskin Balaclava 2

dickssportinggoods.com

$30.00

Just as well-equipped to be worn skiing on a mountain as it is navigating the cold temperatures around the city, the balaclava style is meant for the most intense winter conditions. 

Pro tip: Layer it under your coat and sweater for maximum warmth.

Madewell Chunky Merino Wool Cuffed Beanie

This quintessential beanie’s wide brim allows for a more masculine look, while the speckled knit gives it a touch of trendiness.

Buck Mason Rib Cotton Cashmere Seafarer Beanie

Seafarer knits just look more cozy than any other knit beanies. This black option feels both masculine and fashion-forward to boot.

Beams Plus Fleece Jeep Cap

Comprising classic men’s outerwear fabrics, this textural topper is hands down one of the coolest hats we have seen this year. Wear it to dress up a pair of sweats or throw it on with your freshest suit—the style possibilities are endless.

Vuori The Standard Hat

One of our favorite athleisure brands, it’s no surprise that Vuori also makes some durable caps. Take this no-frills snapback, which can be on the trails, as well as happy hour.

Read more: Best Clothing Brands for Men  

Old Navy Sherpa-Lined Wool-Blend Trapper Hat

Old Navy
oldnavy.gap.com

$20.00

This wool-blend trapper hat is s a sure bet to shield you from whatever weather Mother Nature may throw your way.

Jacquemus La Montagne ‘Le Bob Gadjo’ Bucket Hat

While this style may be slightly intimidating for the hat novices out there, this hat packs just as much warmth as it does style. And while it may be an unconventional winter hat pick, it’s a style flex that we can guarantee will pay off in compliments alone.

Lululemon Fast & Free Men’s Running Hat

Regardless of the season, we always need a go-to workout hat. This one with moisture-wicking and anti-odor technology from Lululemon truly never gets old or goes out of fashion.

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