Style Guide: How to Pick Winter Hats for Men

Whether you can't wait for the first powder of the season or would rather just bundle up and stay cozy indoors, when the cold weather hits you know it's time to break out the winter hat. But just like you wouldn't wear only one pair of pants the entire season, you want to have a few winter hat options that work for any setting or situation. Get the rundown on what to look for in a winter hat, plus ideas on how to play it smart while stepping up your cold-weather wardrobe.

Winter Hat Styles

Baby, it's cold outside. Here are the hottest hats that will help you fight those frigid temps in style.


Beanies

Style Guide: How to Pick Winter Hats for Men - Beanies


Also called a stocking cap or watch cap, beanies are arguably the most popular winter hats for both men and women. Casual, practical, and versatile, these knit beanies are as common a sight on the slopes as they are on the streets.

Often made of natural fibers such as merino wool, cashmere, or cotton, as well as synthetic materials such as acrylic and fleece, these close-fitting caps offer a high level of warmth because they can be pulled close to the head, although the fit can vary from tight-fitting skull caps to the more slouchy beanie style.

If you're going to get a synthetic cap — say, a fleece beanie — look for one with special features such as moisture-wicking, which will draw moisture away from your head. Keep it comfy on the mountain with a Patagonia jacket and winter boots or pair it with your favorite running shoes and The North Face pullover when going about your day-to-day errands.


Flat Caps

Style Guide: How to Pick Winter Hats for Men - Flat Caps


This popular men’s hat style traces its roots to Britain and the U.K., but flat caps are a go-to winter hat in the USA and beyond. Also called an ivy cap or golf cap, a flat cap is noted for having a low profile with a small, stiff brim.

Because they are typically made from wool tweed or cotton, they are a solid choice for keeping your head warm in cold weather. Plus, they instantly amp up your style credentials and offer a dressier option to the more casual beanie.

Newsboy caps, which are a bit puffier and rounder than flat caps, could also do the trick. Check out our guide to newsboy caps and ivy caps to see which hat style speaks to you.

Channel your inner Englishman with a monochromatic ensemble — a grey ivy cap coupled with a wool coat in a similar hue is at once classic and contemporary.


Wool Felt Hats

Style Guide: How to Pick Winter Hats for Men - Wool Felt


Crowned hats such as fedoras, homburgs, and safaris offer polished perfection when stylish winter headwear is at the top of your wish list. Although they are popular as sun hats when made of straw and other lightweight materials, wool-felt versions of these hats are a can't-miss for cold weather thanks to their wider brims and warm fabric.

Signaling a more more formal silhouette and sensibility than beanies or trapper hats, fedoras and other similar toppers should be reserved for dressier winter occasions, not snow sports.

When the mountain hardwear has been left behind, spruce up a cable knit sweater or cashmere cardigan with a wide-brim fedora in a coordinating neutral hue for understated style.


Trapper Hats

Style Guide: How to Pick Winter Hats for Men - Trapper


When the weather outside is frightful, a trapper hat is indeed delightful. Also known as an aviator hat or an ushanka (literally translated as "ear flap hat" in Russian), a trapper hat is characterized by two ear flaps that can either be left hanging or folded back and tied up.

Made from real animal fur such as mink, rabbit, or sheepskin as well as faux fur and other materials, these cold-weather hats offer plenty of protection from the elements. While some might consider the look a bit silly, the important thing to remember is that trapper hats are more about function than fashion.

Tie back the ear flaps "ski style" and pair it with a scarf or neck gaiter, jean jacket, wool parka, or Columbia puffer jacket.

Winter Hat Tips

Now that you know which hat styles are best for the cold season, here are a few top tips when it comes to successfully pulling off your winter headwear.


Spark It Up

Style Guide: How to Pick Winter Hats for Men - Styling Tip

When it comes to beanies and watch caps, don't be shy. Because these knit caps have such a simple shape that's easier to pull off than most other hat styles, feel free to have fun and try bright colors like yellow, orange, red, and green.


Tone It Down


Style Guide: How to Pick Winter Hats for Men - Styling Tips

When selecting a flat clap, fedora, or other hat, remember that darker is dressier. Consider more muted tones such as camel and classic neutrals including black, gray, navy, and brown. Add a pop of color with a scarf, tie, or patterned shirt. Wear it en route to the office or for a fun night on the town.


Get an Earful

Style Guide: How to Pick Winter Hats for Men - Warmth Tips

You could just wear a ball cap in the wintertime, but it won't do the best job protecting you from harsh weather. Try a Stormy Kromer, which is a modified baseball cap with ear flaps. If you just can't bring yourself to rock the flaps, try a heavy jacket with a hood that you can pull over your baseball cap for an added layer of warmth.

Winter Wonderland

Style Guide: How to Pick Winter Hats for Men


There's no reason you have to wear the same cap all winter long. With so many options ranging from casual beanies and Fargo-style trapper hats to dapper ivy caps and fashionable fedoras, the key is knowing which elements are best suited for your purpose and preference.


Whatever you decide, mens winter hats have plenty to offer. Be sure to shop our new arrivals and you’ll be ready to fight the chill in style.


Shop This Style: 8 Floppy Hats You’ll Love

Step up your flair for fashion with these fantastic floppy hat finds.

You’ve Got Mail: How to Ship a Hat

To help you find the easiest and most efficient way to ship a hat, we're taking you through the steps so that both sender and recipient are happy.

Style Guide: How to Pick the Best Winter Hats for Women

Find out what to look for in a winter hat, plus shop the hottest looks so that even when the weather is drab, you'll always look fab.