Holiday Headwear

Holiday headwear brings a festive touch to every celebration, whether you're gathering with family, heading outdoors for winter fun, or simply adding a bit of cheer to your everyday adventures. With styles designed for comfort and lasting value, our collection makes it easy to find the perfect piece for any holiday moment. From classic looks to playful patterns, holiday headwear is ready to help you stay warm, look great, and enjoy every special occasion all season long.

Sort by:

Filter & Sort

504 Items

Adults' Katahdin Pom Hat

A cozy, multi-color beanie crafted from a soft recycled polyester blend for warmth and everyday durability.
Adults' L.L.Bean & Noah Kahan L.L.Beanie

A limited-edition green beanie made from recycled polyester with spandex, featuring a collaborative woven patch.
Adults' Ragg Wool Hat

A thickly knit lambswool hat with soft microfleece lining for warmth, even when wet.

Pros: Not itchy Very comfortable fit Exceptional warmth High quality workmanship Soft fleece lining
Adults' L.L.Beanie, Wide-Cuff

A cozy deep rosewood beanie with a wide cuff, made from soft 100% acrylic yarn.

Pros: Well-made and high quality Perfect size and snug fit Comfortable and cozy Stylish and beautiful colors Extremely warm
Adults' Maine Guide Wool Cap with PrimaLoft, Plaid

A rugged plaid wool blend cap with PrimaLoft insulation and versatile ear flaps for optimal protection.

Pros: Very warm Nice looking Comfortable for winter Good size Well made
Women's Wicked Cozy Knit Pom Hat

A fun putty-colored popcorn-stitch hat lined with ultra-soft recycled polyester fleece for winter warmth.

Pros: Stylish design Attractive print Comfortable fit Cozy and functional Excellent warmth
Adults' Buff Coolnet UV Plus Multifunctional Headwear

A versatile, UPF 50+ headwear in Santana Red, made from recycled polyester with cooling HEIQ technology.

Pros: High flexibility Great multi-functionality Attractive color combination Soft material Good fit
Men's Turtle Fur Rufus Hat

A lambswool-blend hat lined with plush fleece for cozy warmth on trails or in town.
Adults' L.L.Bean Performance Neck Gaiter, Fleece-Lined Print

A blue printed neck gaiter with fleece lining, moisture-wicking stretch fabric, and UPF 50+ sun protection.
Men's L.L.Bean Rechargeable LED Pathfinder Beanie, Plaid
Price was from: $44.95 now: $29.99

A lightweight, plaid beanie with built-in rechargeable LED lighting and moisture-wicking fleece lining.
Women's Heritage Cable Hat

A warm and cozy black cable hat made from a soft wool blend and recycled nylon.
Men's Pistil Willard Beanie

A soft brown beanie crafted from a merino wool blend for warmth and outdoor-inspired comfort.
Men's Pistil Clay II Beanie

A super-soft blue beanie with two layers of cozy viscose/polyester/nylon knit for reliable cold protection.
Women's Boundless Big Pom Hat
Price was from: $29.95 now: $19.99

A cozy, shore rugby striped winter hat with an oversized chunky knit pom, made from 100% polyester.
Women's Turtle Fur Freya Pom Hat

A warm red hat featuring a plush fleece lining and soft, stretchy recycled polyester blend construction.
Kids' L.L.Bean Katahdin Earband
Price was from: $24.95 now: $16.99

A soft, reversible earband in pale turquoise and cool blue, made from recycled polyester and nylon.
Adults' L.L.Bean Sherpa Fleece Beanie

A plush sherpa fleece beanie in shore color, made from 100% recycled polyester for ultra-warmth.
Adults' Pathfinder II Rechargeable Beanie, Camo

A camo-patterned synthetic fleece beanie with built-in rechargeable LED light and moisture-wicking lining.
Adults' Turtle Fur Backcountry Trapper Hat

A luxuriously soft tan trapper hat with cozy earflaps and brim for superior warmth and protection.
Adults' Classic Cashmere Beanie

A luxurious brown beanie crafted from 100% cashmere for exceptional softness and versatile style.
Women's Pistil Nicola Pom Hat

A cozy red wool-blend pom hat with feathered fleece lining and a playful faux fur pom.
Adults' Puffer Cap

A warm, brown insulated cap made from recycled polyester that is lightweight, water-resistant, and windproof.
Adults' Wool-Blend Watch Cap

A warm, chunky ribbed cap crafted from a stretchy merino wool and recycled nylon blend in multicolor.
Women's Heritage Fair Isle Hat

A cozy, warm hat in oatmeal or royal red, made from a durable recycled wool blend.

Holiday Headwear

As the days grow shorter and the air turns crisp, there’s something undeniably special about pulling on a favorite piece of holiday headwear before heading out the door. Whether you’re bundling up for a snowy walk with the kids, joining friends for a tree-lighting ceremony, or simply adding a bit of festive spirit to your errands, the right hat or headband can make all the difference. Holiday headwear isn’t just about warmth—though it certainly helps keep the chill at bay—it’s also about celebrating the season, sharing a smile, and making memories that last. From classic knits that evoke cozy evenings by the fire to playful patterns that bring out the joy in every winter gathering, these pieces are designed to be both practical and fun. Many families have a tradition of gifting holiday-themed hats, and for good reason: they’re a thoughtful, useful present that suits just about anyone, from little ones eager for their first snowball fight to grandparents cheering from the sidelines at a holiday parade.

When choosing holiday headwear, it’s worth considering a few key details to ensure you find something that’s as comfortable as it is festive. Look for soft, itch-free fabrics that offer reliable warmth without feeling bulky, and consider options with thoughtful touches like fleece linings or ear flaps for extra protection on blustery days. Versatility is another plus—styles that pair easily with a variety of coats and scarves can become fast favorites, worn again and again throughout the season. For those who spend a lot of time outdoors, durability and easy care are important, too. A well-made hat or headband should stand up to repeated wear, whether it’s tossed into a backpack for a weekend at the cabin or pulled on for a quick walk with the dog after dinner. And don’t overlook the joy of a little holiday flair—colorful pom-poms, cheerful patterns, and classic winter motifs add a touch of whimsy that’s perfect for the season’s gatherings, photos, and traditions. If you’re looking for something special for the men in your life, you’ll find a great assortment of styles and fits on our Men's Holiday Hats page.

Holiday headwear is also a wonderful way to bring people together, whether it’s matching hats for the whole family on Christmas morning or a favorite beanie that’s become part of your cold-weather routine year after year. These pieces are made for sharing—passed between siblings, borrowed by friends, or tucked into a stocking as a surprise for someone who could use a little extra warmth. They’re easy to personalize with a pin or patch, and just as easy to toss in a bag for impromptu adventures, from sledding hills to ice skating rinks. As you gather with loved ones to celebrate the season, the right headwear helps everyone stay cozy, comfortable, and ready for whatever winter brings. With so many styles to choose from, it’s easy to find something that matches your holiday spirit, whether you prefer understated classics or bold, festive designs. So as the snow begins to fall and the holidays draw near, consider adding a new piece of headwear to your winter collection—or gifting one to someone special—and enjoy the simple pleasures of warmth, comfort, and togetherness all season long.

FAQs

Holiday headwear is often crafted from soft, warm materials like wool, acrylic, fleece, and cotton blends. These materials are chosen for their comfort, durability, and ability to keep you warm during chilly winter outings. Many styles also feature cozy linings or added details like faux fur trims and decorative knits.

To keep your holiday headwear in great shape, gently shake off snow or moisture after wearing, and allow it to air dry if it gets damp. Most knit hats and headbands can be hand washed in cold water with mild detergent, then laid flat to dry. Always check the care label for specific instructions.

Yes, many holiday headwear styles are designed with outdoor activities in mind. Look for features like ear flaps, fleece linings, and snug knits that help block out wind and retain warmth, making them a great choice for sledding, hiking, or winter walks.

Absolutely! Holiday headwear makes a thoughtful and practical gift for people of all ages. With a wide variety of styles, colors, and patterns available, it’s easy to find options that appeal to kids, teens, adults, and grandparents alike.

Adding a personal touch to holiday headwear is simple—consider embellishing with a favorite pin, festive patch, or even a handmade pom-pom. Some people like to coordinate colors or patterns with family members for group photos or special occasions, making the season feel even more memorable.

It's time to upgrade your browser

Holiday Headwear