13 Best Winter Hats for Men According to a Canadian

I’m a long-time Patagonia fan, and this beanie has become my favorite hat to get through Canadian winters.

Made from a blend of recycled nylon and recycled wool, it’s both ultra-warm and incredibly durable. The fit starts off nicely snug but conforms to your unique head shape the more you wear it. Once the fibers fully relax, it’s guaranteed to be the most comfortable beanie you’ll own.

For those viciously cold, well-below-freezing days, this is my go-to beanie. The recycled Pertex Quantum ripstop shell is ultra-tough and windproof, and the 650g goosedown (responsibly sourced, of course) maximizes warmth retention.

The hat is designed to roll up small enough you can stuff it into any backpack or pouch to take it anywhere and everywhere. It’s even light and compact enough to wear beneath a ski or snowboarding helmet.

American designs meet Japanese craftsmanship, and I’ve found the result to be wonderful. Each of these beanies is crafted in Japan using quality Japanese fabrics, but the American fisherman beanie style makes it the ideal finishing touch to your Western winter outfit or ski suit.

The addition of Spandex into the acrylic-wool-nylon-blend fabric gives it just the right amount of stretch to be versatile enough for any sports or athletic use.

Vuori makes some of my favorite athleisure pieces and lounge pants, and this beanie skews heavily toward the latter.

Though it’s made using 70% wool—so it’s tough as nails and sports-friendly—the addition of 30% cashmere makes it both more delicate and cloud-soft. It’s the ideal hat to wear when heading out on a date night or weekend hangout with friends. You’ll always be comfy and look stylish in this gorgeous hat.

Minimalist design meets sport-friendly comfort. Cut in the watch cap style, it’s on the sleeker side, crafted to cling to your head without the need for a brim.

The acrylic fabric feels soft as cashmere against your scalp, but has the durability you need for outdoor winter work and adventures. Best of all, it features a featherweight microfleece liner that won’t add significant heft but drastically improves warmth-retention.

If you want a hat that prioritizes both form and function in equal measure, I strongly recommend this one.

The wool used for the hat is durable, moisture-wicking, and thermoregulating, perfect for winter running, snow sports, or outdoor work and it won’t get soggy or sweaty. However, it’s built with that touch of elegance that makes Billy Reid one of my go-to menswear brands when I want to dress up.

Winter runners, this hat’s for you. It’s crafted using pure Merino wool, an ultra-durable fabric that will conform to your head, trap in body heat, regulate your temperature, and wick moisture away from your skin.

The two-gauge construction ensures it fits snugly but won’t constrict your head. It’s also beautifully easy to style; wear it with any puffer jacket, or thermal base layer.

For a hard day’s work on any job site or farm, this is the beanie for you. Built for contractors, lumberjacks, and outdoorsmen, it’s tough as nails and versatile enough for any job.

The tight knit does an excellent job of trapping in body heat, but you’ll find it still breathes and flexes with you even over long hours of hard labor. Comfy, cozy, and tough—just what you want.

I’d never tried pure virgin Italian wool before, but once I slipped this cap on, I fell in love.

It’s wonderfully soft and surprisingly warm, but my head never overheated even when I took it snowboarding or cross-country skiing.

It’s slim enough to fit beneath a helmet, but it still offers excellent warmth retention if I’m wearing it alone. Thanks to the folded brim, I can easily adapt it to fit my over-sized head.

Keep it simple and affordable with this watch cap-style hat. Made from a tough, ultra-warm tight-knit acrylic fabric, it’s a hat that’ll last for years of winter sports, work, and outdoor adventures.

The iconic watch cap design makes it easy to pair with everything from your winter parka to a light fall chore coat. For those who want only American-made goods, this is my recommended hat.

For the working man, I’d recommend this Carhartt beanie every time. Both my welder and mechanic sons love theirs (a Christmas present two years back).

It manages to be light, warm, and ultra-tough all at once. The acrylic fibers have enough stretch that they can easily tuck away their long, curly hair beneath to keep it out of the cold, but it’ll still hug their scalps snugly for a comfy fit.

If you’re headed to the ski slopes or out on a cross-country winter run, you’ll want this winter beanie for sure.

I love how the interior is insulated with an ultra-warm polyester fleece that traps body heat close to your scalp so no winter wind or snowstorm can chill your head. Thanks to its polyacrylic fiber shell, it’s tough enough to stand up to both sport and work.

A beanie and a cap? Yes, please! The hat is as versatile as any beanie, but the addition of a cap brim shields your eyes from wind, rain, sleet, and snow.

There’s also stow-away ear flaps that you can pull down when you want extra protection, and the acrylic-and-wool-blend exterior with thermal furry fleece inner lining does an amazing job of keeping out even the worst winter cold.