15 Winter Hats for Men That Will Look Sharp in Harsh Weather

Let's face it: It's the go-to for a reason. The Carhartt Watch Cap has taken on almost a cult status these days, particularly after no less than Rihanna herself was spotted sporting one.

This simple beanie is a comfortable cap that provides ample warmth for most wearers, and can work with almost every casual outfit without clashing. 

More: You Can't Go Wrong With One Of These Seriously Stylish Men's Beanies

Russia has given the world many great contributions: War & Peace. The songs of Stravinsky. The plays of Anton Chekhov. Chekhov on Star Trek. The list goes on.

But perhaps their finest innovation is the ushanka, the warmest winter hat this side of the Moskva River. The famous fuzzy hat with deployable ear flaps can offer warmth in even the harshest conditions, and this particular hat even offers an attachable face covering to help keep the wearer safe from windchill.

Some winter hats can be functional beyond just basic warmth. This LED Beanie sports a bright light on its brim to help illuminate your path in those dark winter hours, and it will make sure you're visible to vehicles during late night jogs. Plus, in the daylight, you still have a stylish gray skullcap that's the perfect conversation starter.

More: 14 Running Hats to Keep Your Noggin Warm This Winter

Whether you've binged Peaky Blinders or obsessed over '70s Springsteen, every man has at least once looked at a flat cap and thought, “Could I pull it off?”

This winter is the perfect time to find out! Not only does the flat cap — or “newsboy hat” — have a rich history that dates back to the 14th century — when Englishmen had to wear a wool cap on Sundays or be fined — but it's also the perfect way to keep your head warm in a look that's never gone out of style.

Whether you're one to go for a winter run, or it falls on you to shovel the walkway every snowfall, this the cap if you live by LL's adage that you “can’t live without my radio,” or more likely in this case, your music streaming service.

The SoundBot HD Smart Beanie makes it easy to keep your favorite tunes on you at all times, without risking your earbuds slipping into a snowbank. That's because this beanie has built-in bluetooth speakers, delivering HD sounds that you can control with the buttons discreetly hidden on the hat's label.

If bike riding is part of your winter routine, you'll want to be sure to protect your face from the elements — and keep your head warm while you do it.

That's where the Tough Headwear Helmet Liner Beanie comes in. An Amazon's Choice for men's cycling caps, this comfortable beanie fits perfectly under any standard bike helmet, and has an attached face shield that also functions as a neck warmer when worn below the chin.

OK, so there are cases where we'll highlight a certain winter hat because it best serves a very specific purpose. And that's the case here too. What's this Balenciaga Wool-Blend Beanie best for? For treating yourself, that's what.

With the winter comes holidays, travel, and so many opportunities to be social. So take the chance to show off with one of the most iconic names in style emblazoned across your beanie!

If you have to contend with the coldest winds winter has to offer, then you likely want the most coverage available.

For that, we recommend a reliable balaclava — particularly, this stylish one from Stone Island. Some cheaper balaclavas can leave you looking like a comic book super-criminal, but a carefully crafted, full-coverage cap will having you looking sharp in even the harshest conditions.

You’ve heard the old adage “It’s what’s on the inside that counts,” and that’s true for winter hats as well. After all, it doesn’t matter how fashionable it is if it’s not keeping you warm.

For the coziest cap ever, take a look at this Polar Extreme beanie. Thanks to its fleece interior lining, this hat will most definitely keep your head warm. The material also wicks away sweat from your scalp, resulting in optimal comfort.

Not into the knitted skullcap style? Then look to what men wore in the winter before the beanie was invented. 

From Minnesota to Madison Avenue, when businessmen needed to work in the winter, they relied on a stylish wool fedora. After all, it was Sinatra's go-to hat for when the weather outside got frightful. And if it's good enough for the Chairman of the Board ... well, it's definitely good enough for you.

Since 1994, Smartwool has been making winterwear designed by skiers, for skiers. So it stands to reason that they knew what they were doing when they designed this cuffed beanie.

Heavily insulated with 100% merino wool fabric, this beanie's double-knitting makes for a comfortable fit whether you’re out on the ski slopes or sipping some cocoa.

Don't associate cowboy hats with cold weather? Then you should watch McCabe & Mrs. Miller. The truth is, the felt cowboy hat we all consider the standard was originally meant just for winter nights  —in fact, cowboys favored lighter star hats in the summer.

Now, if you're looking for a reliable cowboy hat to weather the winter wherever you are, you might as well go with the the gold standard — a Stetson. With a sturdy build and quality material, it'll keep you warm no matter whether you're cattle-wrangling or commuting.

If you're planning on skiing or snowboarding (or have any other helmeted activities on your agenda for this winter), don't forget a winter hat to combat the cold. But while most knit beanies can be cumbersome under some properly secured headgear, this skull cap made from polyester and lycra will wick away sweat and offer strong thermal retention — all while feeling like you're wearing nothing at all.

Let’s face it: As men, it’s hard to find the right style of hat that works. And once some guys have found it, that’s what they stick to — no matter what.

So if you’re a baseball-cap man who’s committed to solely being a baseball cap man, there’s no reason for your scalp to get cold for the sake of your signature style. Get yourself this woolen tweed cap so you can stay “on brand” without getting frostbitten in the process.

Maybe you're not one for classic outdoor winter sports. In that case, you don't need the latest sweat-wicking tech or intense thermal retention. Maybe you plan to spend most snow days inside playing video games.

Let your winter wear let everyone know you'd much rather battle snow pokies than shovel snow by sporting this Super Mario Peekaboo Beanie. The warm red cap features the iconic plumber popping up just over the brim. And before you ask, yes, there's a Luigi option, too.