Men's Holiday Hats

Men’s holiday hats bring a festive touch to every celebration, whether you’re gathering with friends around the fire or heading outdoors for winter adventures. With classic styles and cheerful details, these hats are designed to keep you comfortable and in the spirit all season long. Explore options that add warmth and a bit of holiday cheer to any outfit—perfect for everything from snowy strolls to family get-togethers. Find men’s holiday hats that make every moment outside even more memorable.

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504 Items

Men's Stetson Sturgis Crushable Wool Hat

A crushable wool felt hat in cordova that retains shape, featuring a Dri-Lex® sweatband and 3¼" brim.

Pros: Durable Good fit Comfortable Soft fabric Stylish appearance
Adults' L.L.Bean Trucker Hat

A classic trucker hat with original artwork, breathable mesh, cotton brim, and adjustable snap back.

Pros: Great look Attractive design Nice souvenir Solid quality
Adults' Stetson Expedition Crushable Wool Hat

A lightweight, weather-resistant wool hat with a 3" brim and Dri-Lex® sweatband, made in the USA.

Pros: Perfect fit Traditional styling Stylish Practical
Adults' MIF&W Waxcloth Hat, Brook Trout

A forest green, water-resistant cotton/nylon hat featuring an embroidered Maine brook trout and MIF&W logo.
Adults' Bean Bright Multisport Hat

A neon yellow, breathable running cap with 360-degree reflectivity and dual mesh panels for ventilation.

Pros: True to size Breathable material Comfortable fit
Adults' L.L.Bean Camouflage Trucker Hat
Price was from: $29.95 now: $24.99

A comfortable trucker hat with a mossy oak camo design, featuring a breathable polyester mesh back.
Men's Pistil Trent Sun Hat

A lightweight green nylon sun hat with UPF 50+, moisture-wicking band, and ventilating mesh panels.
Adults' No Fly Zone Baseball Hat

A deep olive, lightweight hat with insect-repellent treatment, UPF 50+ protection, and moisture-wicking CoolMax sweatband.
Adults' No Fly Zone Boonie Hat

A lightweight, slate-colored sun hat with UPF 50+ protection and insect-repellent treatment for outdoor adventures.
Men's Pistil Fiji Sun Hat

A handwoven tan sun hat crafted from papyrus with a leather chin strap and canvas trim.
Adults' Beanlight Floating Trucker Hat
Price was from: $24.95 now: $16.99

A multi-color floating trucker hat with mesh back and foam construction, crafted from durable synthetic and nylon.
Adults' L.L.Bean Heritage Hunting Hat

A low-profile dusty olive hunting hat made from soft washed-chino twill with an adjustable cam-lock strap.
Adults' MIF&W Waxcloth Hat, White-Tailed Deer

A tough, water-resistant canvas hat featuring a white-tailed deer and MIF&W logo, in forest green.
Men's Signature Baseball Hat

A brown cotton corduroy and chamois baseball hat with a heritage-inspired design and embroidered logo.
Adults' Katahdin Pom Hat

A cozy, multi-color beanie crafted from a soft recycled polyester blend for warmth and modern style.
Men's Aussie Breezer Hat

A khaki sun-protection hat with UPF 50+, mesh side panels, and adjustable fit for maximum comfort.
Adults' L.L.Bean Performance Beanie

A black, moisture-wicking beanie with fleece lining and UPF 50+ protection, ideal for winter activities.

Pros: Fits well under a jacket hood High-quality fabric Lightweight design Excellent warmth Comfortable fit
Adults' L.L.Bean SunSmart® Straw Hat
Price was from: $54.95 now: $39.99

A lightweight, unisex straw hat with UPF 50+ protection and a 3.75-inch wide flexible brim.
Adults' Cotton Bucket Hat
Price was from: $32.95 now: $24.99

A classic blue bucket hat made from lightweight cotton twill with a sun-shielding brim and mesh sweatband.
Adults' Classic Cashmere Beanie

A luxurious brown beanie crafted from 100% cashmere for exceptional softness and versatile style.
Adults' Wharf Street Rain Hat

A lightweight yellow rain hat with a wide brim, waterproof recycled nylon shell, and adjustable drawstring.
Adults' Mountain Classic Bucket Hat
Price was from: $39.95 now: $29.99

A lightweight, recycled synthetic bucket hat offering UPF 50+ sun protection and breathable, weather-resistant comfort.
Adults' Cotton Corduroy Bucket Hat

A classic brown corduroy bucket hat made from 100% cotton twill with a sun-blocking brim.

Men's Holiday Hats

As the holidays approach and the chill settles in, a dependable hat becomes more than just a practical accessory—it’s a welcome companion for every winter adventure. Whether you’re heading out to cut a fresh tree, catching up with family around a crackling backyard fire, or simply taking a brisk walk through town, the right hat helps you embrace the season with comfort and style. Men’s holiday hats are designed to keep you warm and comfortable, offering lasting value with classic details and sturdy construction. From timeless knits to rugged trapper styles, these hats are made to stand up to cold days and frosty evenings, providing the kind of cozy coverage you can count on year after year. The holidays are filled with moments spent outdoors, from early morning errands to festive gatherings under twinkling lights, and a well-made hat ensures you’re always ready to enjoy them, no matter what the weather brings.

Holiday hats don’t just solve the problem of cold ears—they bring a sense of tradition and togetherness to the season. They make thoughtful gifts for dads, brothers, friends, and colleagues, offering a practical touch that’s also personal. There’s something special about unwrapping a hat that’s built for warmth and adventure, especially when it’s crafted with comfort in mind and designed to look just as good by the fire as it does out in the snow. For those who love the outdoors, these hats are a staple for everything from winter hikes to sledding with the kids. And for anyone who prefers to keep things simple, the easy-to-wear styles fit seamlessly into everyday life, pairing well with everything from a favorite jacket to a cozy sweater. With so many options—classic beanies, fleece-lined caps, and earflap hats among them—it’s easy to find one that suits your needs, whether you’re looking for something to wear on a weekend getaway or just around the neighborhood.

Choosing the right holiday hat comes down to a few key considerations: warmth, comfort, and versatility. Look for hats that offer soft, itch-free materials and a fit that stays put without feeling restrictive, so you can focus on the fun at hand. Durable construction means your hat will hold up through countless snowball fights and winter walks, while timeless styles ensure it never feels out of place, season after season. If you’re shopping for someone else, consider what they enjoy most about winter—maybe it’s spending hours outdoors, or maybe it’s gathering with family for a holiday meal. Either way, a quality hat is a gift that brings warmth and cheer long after the decorations are packed away. And if you’re looking to round out your cold-weather wardrobe, don’t forget to explore other seasonal favorites, like those featured on our Fall Hats For Men page, for even more inspiration on staying comfortable and prepared as the weather turns colder.

FAQs

Men's holiday hats are often made from high-quality materials designed to provide warmth and comfort during colder months. Common options include wool, fleece, acrylic, and cotton blends. These materials are chosen for their durability, softness, and ability to retain heat, making them ideal for winter activities and festive gatherings.

Yes, many men's holiday hats are designed specifically for outdoor use. They offer features like ear flaps, fleece linings, and wind-resistant fabrics to help keep you comfortable during winter walks, snowball fights, or evenings around the fire. Their durable construction ensures they can handle the rigors of outdoor adventures.

Absolutely. The versatile styles of men's holiday hats mean they pair well with a wide range of outfits. Whether you're heading out in a cozy sweater and jeans or dressing up for a holiday dinner, you can find a hat that complements your look while keeping you warm.

Men's holiday hats are a thoughtful and practical gift choice. They offer comfort, warmth, and a touch of seasonal style, making them ideal for friends, family members, or colleagues. Their timeless appeal ensures they’ll be appreciated and used for many winters to come.

To maintain the look and feel of your men's holiday hat, follow the care instructions provided on the label. Many hats can be hand washed in cool water and laid flat to dry, while others may be suitable for gentle machine washing. Regular care helps preserve the hat’s shape, color, and softness throughout the winter season.

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Men's Holiday Hats