5 Types of Winter Hats: Which is Right For You?

It’s getting cold outside, and there is no way around it: You need to wear a hat. No amount of proper layering will warm the chill just north of your shoulders, so keep your head warm in style. Here is your Cheat Sheet guide to your winter hat wear that won’t only keep you warm all season, but fashionable too.

The trapper hat

trapper hat

Source: Kohl’s

This one is one of our all time favorites — it’s warm and exudes confidence. Just a little historical background on the Trapper Hat: It’s formally known as an ushanka, which originated in Russia, is also sometimes called “Elmer Fudd,” like the lovable Loony Tunes Character. The hat is constructed with two flexible flaps, one on each side, with a string or leather tie that can connect the flaps either beneath the chin or on top of the hat. Although there are a variety of styles, any good ushanka, according the The Art of Manliness, should include the following:

  • flexible ear flaps on each side of the hat
  • a nice, thick fur lining, often both outside and inside
  • three default positions to the hat: open (flaps tied on top of the head), closed (flaps tied together beneath your chin), and loose (flaps are left hanging)

While most of the hat styles are brimless, there are some that include an “eye flap” or a small visor to keep your forehead warm, while also keeping the sun out of your eyes. This hat is ideal if it’s unbelievably cold outside or if you’re going to be outside for an extended period of time. Try the Apt. 9 Trapper Hat from Kohl’s.

The newsboy cap

Source: J. Crew

The newsboy cap is a fantastic go-to hat that is best worn with a more formal business outfit. For winter, this flat wool cap is best worn in a thicker wool. Although it’s a cold-weather option, and you’ll certainly look stylish wearing it, if it’s bitterly cold outside, because there are no flaps to keep your ears or neck warm, it’s insufficient if you’re going to be outside for a long period of time. If you must wear it, make sure you’re set to go with a thick, wool scarf. Try the English Wool Newsboy Cap from J.Crew.

The fur felt fedora

bronson, hat

Source: All Saints

The felt fedora is the classic gentleman’s hat, with a ton of history behind it. The fedora comes in various brim lengths, so if you’re not into a wider brim, you may want to skip this one, or get a little out of your comfort zone and give it a try. This classic menswear item looks great dressed up or down. Some of the more modern style fedoras, specifically designed for the cold weather, come with a semi-circular ear warmer in the same color as or in a complementary pattern to the hat. It is either tucked up inside the crown or detachable. Let’s face it: During the winter months, you need all the ear protection you can get. Although it might disturb the aesthetic of the hat, you won’t care when the thermometer drops below freezing. The fedora will continue to remain the standard. Try the Bronson Leather Fedora Hat by All Saints.

The Stormy Kromer hat


Stormy Kromer

According to The Art of Manliness, the Stormy Kromer hat originated from a train engineer with the same namesake. The man with the last name Kromer needed a hat that would keep his head warm and wouldn’t wouldn’t blow off when he stuck it out the train window. Similar to a baseball cap, it’s a six-panel design is intended to keep your head warm during even the fiercest winds. Today, Stormy Kromer hats are still hand-sewn in the U.S. are a distinct form of casual headwear. Try The Original Cap by Stormy Kromer.

The beanie


Source: Coal

Simple and made from a variety of fabrics, the best one to opt for during the winter months is one that is wool or made of a mixed wool blend. Meant to fit the head perfectly, with extra fabric hanging off the top, this all-time favorite can dress down or add interest to an outfit immediately. Try The FLT by Coal.

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