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30 stylish winter hats that will keep you warm all season long

Top things off with the perfect outerwear essential.
Carhartt Knit Cuffed Beanie, LC Lauren Conrad Birdseye Pom Beanie, Kangol Wool Lahinch Bucket Hat, Under Armour Around Town Beanie
TODAY Illustrations / Dick's Sporting Goods / Kohl's / Amazon

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December always feels a little bit like a lighthearted rehearsal for winter. Then comes January, when the frigid temps and seasonal blahs start to set in. If you’re going to invest in one new piece of clothing this month, consider a nice, warm hat.

Many of us are still spending more time than usual outside this year, so it's truly a practical winter fashion item. And perhaps, just as importantly, a new topper can be a psychological pick-me-up during a loooong winter.

Whether you’re going for an après-ski vibe, urban chic or — let’s be honest — you just want to look good for a quick trip to the grocery store, these cold weather essentials are sure to garner countless compliments.

Classic beanies

Yummy Sweater Co. Beanie

A basic black beanie is a must-have for winter. Its thick weave will keep you warm on the coldest days.

Gap Sherpa Beanie

This textured model is big on super-softness and style. Available in purple, black and brown, it's perfect for staying cozy and concealing a two-day-old blowout.

Mango 100% Cashmere Beanie

There's nothing like cozy cashmere to keep you warm in the winter. It comes in two classic colors that are perfect for everyday wear: medium brown and light heather gray.

Artizia Brock Beanie

This beanie — in a goes-with-everything brown color, turn-up brim and knitted yarn style — will be your cold weather go-to.

Anthropologie Embellished Flourish Beanie

For a dressy, uber-feminine turn, try this wool/nylon blend embellished with floral accents.

Carhartt Knit Cuffed Beanie

Cover up helmet hair after a long day of skiing, or just transition from work to home in style with this turnback beanie from Carhartt.

Quince Mongolian Cashmere Slouchy Beanie

Finding a beanie with just the right amount of slouch can be tricky. But this affordable cashmere topper — available in five sleek hues — nails a pulled-together-but-didn’t-try-too-hard look.

Under Armour Around Town Beanie

It’s affordable, available in six flattering shades and machine-washable. It’s no wonder Under Armour fans love this versatile hat.

Naadam Signature Ribbed Cashmere Beanie

Whether you’re running errands around town or braving a walk in the woods, you’ll get major style points with this luxurious, splurge-worthy cashmere beanie.

Barca Slouchy Fleece Lined Hat

This simply slouchy beanie is the perfect option to transition from city to the slopes seamlessly. We can’t promise you won’t get hat hair, but you’ll look so good you won’t even care.

Pom pom beanies

Gap Factory Cable Knit Beanie

This cable knit beanie with a playful faux fur pom-pom also comes in black and white.

LC Lauren Conrad Birdseye Pom Beanie

Whether or not you believe the old statistic that a crazy amount of your body heat is lost through your head, you can’t get cozier than this luxe knitted cap from Kohl's.

Ugg Knit Beanie

Bundling up for freezing winter weather is, in large part, not a good look. But this plush pom will distract from even the most unflattering winter ensembles and get you noticed — in a good way.

Banana Republic Factory Pom Beanie

Put a star on top with this winter white stunner. It comes in three colors and, right now, you can take it home for 40% off.

Fenical Metallic Beanie

One word for this topper: showstopper. With a get-noticed metallic silver color, you’ll brave the elements in style — and with shiny, bright expectations for 2022.

Chic Tweak Knit Beanie

If you have problems committing, try this customizable hat with mix-and-match faux-fur pom colors. How it works: You simply snap the poufs on and off to change your look.

Athleta Ribbed Pom Beanie

With chunky ribbing and a chic turnback, this little number proves that classic never goes out of style.

Turtle Fur Snowfall Beanie

Ubiquitous outerwear brand Turtle Fur is a winter go-to because of their thoughtful designs and universally cute styles. This hat is no exception: Its ultraluxe fleece lining is crazy-warm and the nobbly weave and cute pom add a feminine spin.

Obermeyer Durango Faux Fur Pom Beanie

If your look is more fair isle than fancy, try this quintessentially winter hat.

Bucket hats

The North Face Cragmont Bucket Hat

Whether you love them or hate them, bucket hats are everywhere this year. This cold weather version in textured green is the perfect balance of function and fashion.

Outdoor Research Quinn Bucket Hat

Another textured option, this top-rated style features an added bonus: A small zippered pocket that can fit a key, some cash or a small treat for later.

Roxxi Faux Fur Bucket Hat

Fashion favors the bold, right? Rock this iconic silhouette in a cheerful, get-noticed color and pattern combination.

MaxNova Fuzzy Fleece Faux Fur Bucket Hat

Choose from over a dozen playful patterns and designs with this bestselling bucket hat.

Tessa Short Reversible Bucket Hat

This bucket hat does double-duty with faux Sherpa on one side and leather on the other. The two styles can work with any look you're going for.

Ugg x Telfar Bucket Hat

Telfar, the popular shopping bag brand with drops that sell out in minutes, recently collaborated with Ugg to create a line of super cozy and trendy pieces. The collection includes pieces like this bucket hat with a faux-shearling trim.

Urban Outfitters Wide Wale Corduroy Bucket Hat

Have fun with different materials and textures for your bucket hat. Corduroy, while most often seen in jackets and pants, are a great way to add another dimension to your look in bucket hat form.

Levi's Quilted Bucket Hat

Match your hat with a quilted coat to create a cohesive look. Seasonal weather and trend changes are no match for this timeless quilted style.

Guess Faux Fur Bucket Hat

A simple black faux fur bucket hat is an easy way to add a dressy element to any outfit. Whether you're dressing up or keeping it casual, the hat speaks for itself.

Kangol Wool Lahinch Bucket Hat

Think of this as a throwback piece that never really went out of style (thank you, LL Cool J). Kangol’s sporty-meets-streetwear winner comes in four colors.

Shein Solid Plush Bucket Hat

This well-priced hat comes in over a dozen gorgeous colors. We particularly like the khaki plush because it has a high-end, real shearling look.

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