The 20 Best Winter Hats for Men, From Loro Piana to L.L.Bean

Winter is coming—and in some areas, it’s already here. With the halcyon days of summer a thing of the past, it’s now time to bust open our wardrobes and make sure we have all the gear we need to comfortably, cozily get through the cold months. And having the best winter hats in our rotation is key.

Finding the right winter hat for men can be tricky. Options abound, from woolen baseball caps reminiscent of their cotton cousins we might wear in the summer to shearling-lined trapper hats for the coldest climates. It largely comes down to personal preference, as well as an understanding of just how cold you tend to run in the winter months—and what your environment is going to be like. Do you necessarily need a full-on balaclava? Or will a lightweight hat to go from outdoors to indoors be sufficient?

More from Robb Report

To help you find the best hats, we’ve curated twenty of our favorites, all of which will help keep your head and ears nice and toasty this winter.

Best Stylish Hat for Winter

Loro Piana Logo-Appliquéd Storm System Cashmere Beanie

Invest in quality with this water-repellent beanie from Loro Piana that has a look all its own, made from the highest quality cashmere.

Buy Now on Mr Porter: $495

Best Baseball Cap for Winter

Brunello Cucinelli Logo-Embroidered Cashmere and Silk-Blend Baseball Cap

Paging Kendall Roy. If Brunello makes it, you know it’s good. This luxurious hat has the unassuming look of a baseball cap, but is expertly crafted from the highest-quality cashmere and silk blend, featuring an adjustable leather black tab, making it perfect for catching a helicopter in the cooler months.

Buy Now on Mr Porter: $650

Best Headband for Winter

Smartwool Intraknit Merino Tech Headband

This piece combines the performance of merino wool—it’s lightweight, temperature-regulating, antimicrobial, so it doesn’t stink—with 3D knitting technology. Targeted mesh ventilation gives this style a great amount of breathability, along with a snug performance fit, making it a versatile piece if you’re going on any outdoor adventures this winter.

Buy Now on Smartwool: $35

Best Fair Isle Knit Hat for Winter

Dale of Norway Merino Wool Hat

When in doubt, go with a classic. Dale of Norway has been the authority on Norwegian-style fair isle knits for decades, and this substantial merino hat combines that heritage look with a high degree of comfort and warmth.

Buy Now on Amazon: $70

Best Watch Cap for Winter

Norse Projects Watch Cap

The term “watch cap” refers to a snug-fitting beanie that historically has been favored by sailors and farmers for its no-nonsense, never-budges fit. This Norse Projects iteration is made from a soft, yet warm blend of cotton and wool, perfect for those who prefer an authentic look with a much gentler touch.

Buy Now on End. Clothing: $80

Buy Now on Norse Projects:110

Best Workwear Beanie for Winter

Carhartt WIP Logo-Appliquéd Knitted Beanie

Normcore, cottagecore: Call it what you want. Carhartt has those trends, grounded in workwear, cornered. And this knitted, cuffed beanie is no exception. It’s made from a sturdy acrylic yarn that can be thrown in the washing machine to remove whatever grime you throw at it, andit comes in a range of colors. At $50 a pop, you can’t afford to not have a few of these in rotation.

Buy Now on Mr Porter: $50

Best Retro-Inspired Hat for Winter

Filson Double Mackinaw Wool Cap

This hat is a perfect indication of what Filson does best—taking something heritage and making it feel current and cool. This naturally water-repellent Mackinaw wool cap features a perfectly proportioned 3-inch bill, which protects your face from rain and snow without sacrificing visibility. The insulated crown features tie-back shearling-lined ears and neck flaps to keep your head and neck warm and dry when the going gets tough.

Buy Now on Filson: $150

Best Western-Style Hat for Winter

Nick Fouquet Disfarmer Hat

If you’re heading out west this winter and looking for the best hat, look no further. MillinerNick Fouquet is known for his gorgeous hand-finished toppers, and this one comes in a substantial suede material with a plaid lining under the brim. Whether you’re kicking back at the Yellowstone Club in Big Sky or jockeying for a table at Cloud Nine in Aspen, this is the hat to do it in.

Buy Now on The Webster: $1,680

Best Cashmere Beanie for Winter

The Row Dibbo Hat in Cashmere

How are those Olsen twins so damn good at everything? You’ve never felt true luxury cashmere until you’ve held this Dibbo Hat in your hands—it’s chunky, impossibly thick and substantial and it’s cool enough to wear in the city or on a mountainside, without being showy. It’s a beanie that feels like a million bucks.

Buy Now on Mr Porter: $590

Best Everyday Beanie for Winter

Patagonia Everyday Beanie

Not too snug, not too slouchy, not too warm, not too ventilated: Patagonia’s Everyday beanie gets it just right. Plus, it’s made from partially recycled materials and it’s Fair Trade Certified.

Buy Now on Rei: $39

Most Durable Hat for Winter

Stio Fremont Beanie

Stio—a brand based in Jackson, Wyoming, and a favorite amongst hardcore skiers everywhere—is the perfect companion for all your outdoor pursuits. It’s made out of the brand’s popular Karuishi stretch fleece that provides warmth and breathability for biking, ski touring and all your high-intensity pursuits. This hat, which is machine washable, will continue to look crisp and cool after many wears and many rounds through the washer.

Buy Now on Stio: $45

Best Trapper Hat for Winter

Barbour Morar Wax Trapper

If high-tech-looking hats are less your speed, consider this trapper hat from Barbour, which has been making reliable pieces for inclement weather conditions for nearly 130 years. Crafted from the brand’s signature waxed cotton, this rugged, weather-resistant piece is great for climates where you need serious warmth in the dampest, snowiest conditions.

Buy Now on Backcountry: $70

Best Sherpa-Lined Hat for Winter

L.L. Bean Sherpa Five-Panel Hat

Take a turn on the retro side of winter hats with this sherpa-lined baseball cap from all-American favorite L.L. Bean. If your head gets sweaty and you prefer a little ventilation over the ears, this is the style for you.

Buy Now on L.L.Bean: $40

Best Pom-Pom Hat for Winter

Thom Browne Merino Aran Cable Stripe Pom Pom Hat

Every man needs a pom-pom hat in his winter arsenal. They’re playful and fun. The way to pull it off without looking like a child is to purchase one that’s high-quality, with just enough street cred. This Thom Browne option hits the mark, made in Italy from 100 percent virgin wool, and emblazoned with Browne’s signature stripe detail over the crown.

Buy Now on Matches Fashion: $350

Best Logo Beanie for Winter

Balenciaga Allover Logo Beanie

Logomania is reaching its peak, and if you’re going to dip your toe into this trend, there’s no cooler brand with which to do so than Balenciaga. Not only does this hat streamlined and feels of-the-moment, it’s also made in Italy from a thick wool knit that delivers serious warmth.

Buy Now on Balenciaga: $425

Warmest Hat for Winter

Canada Goose Thermal Toque

Introducing the expedition-grade toque that doesn’t look like an expedition-grade toque. Made from three thick, strategically knit layers that lock in heat and are treated with a water-resistant finish, this hat works as well in the Arctic Circle as it does for the chilliest commutes in the city.

Buy Now on Canada Goose: $250

Best Balaclava for Winter

Outdoor Research Gorilla Gore-Tex Infinium Balaclava

Don’t mess around when it comes to winter cold and precipitation. Balaclavas have been trending on the runways for several seasons now, and this high-performing option from Outdoor Research provides all the functionality and warmth you’ll need to stay warm and dry on your next venture outdoors. It features a soft fleece interior and a weather-resistant shell, as well as a removable breathing port so you can tailor your protection to the day’s conditions as needed. We would, however, suggest not wearing this one to the bank.

Buy Now on Outdoor Research: $60

Best Bucket Hat for Winter

Aimé Leon Dore Heritage Wool Bucket Hat

Bucket hats are having a moment, and this option from Aimé Leon Dore combines the fashion-favorite silhouette with a classic heritage wool design. Best of all? It’s machine washable—so you can rock the trend and then easily wash it at the end of the season.

Buy Now on Aimé Leon Dore: $60

Best Wool Hat for Winter

J.Press Shaggy Dog Cuffed Hat

You know and love J.Press for, among many other things, their iconic Shaggy Dog sweaters—and this hat version is just as lovable. It’s made from a just-fuzzy-enough, 100 percent brushed Shetland wool, made in Scotland. Pro tip: Buy a coordinating Shaggy Dog sweater so you can match.

Buy Now on J.Press: $60

Best Winter Hat for Outdoor Exercise

Velocio Zero Cycling Cap

Winter hats for outdoor activities are a conundrum—it’s difficult to find one that provides warmth and weather resistance, because the ones that are overly insulated tend to retain too much heat and sweat, which can instantly turn your head cold in the midst of even the most intense activities. This cycling cap manages to do it all while maintaining excellent breathability. It can be easily layered under a helmet for cycling pursuits or worn on its own as a winter running or cross-country skiing accessory.

Buy Now on Velocio: $89

Best of Robb Report

Sign up for Robb Report's Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.

Click here to read the full article.