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Winter Hats

Warm, easy-to-wear styles for cold days and winter road trips.

Our winter hats are designed to move easily between indoors and out — warm without feeling heavy, and comfortable wherever the road takes you.

Trusted by 100,000+ customers worldwide · 4.9★ average rating

Shop All Winter Hats

23 Results

Dusty Brown | Packable Outback Hat
best-seller
New

Dusty Brown | Packable Outback Hat

5.0 (22)

$234.00

Unit price
per 

2 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Dusty Olive Espresso | Packable Outback Hat
best-seller
New

Dusty Olive Espresso | Packable Outback Hat

4.8 (10)

$234.00

Unit price
per 

2 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Toby Black | Fisherman Beanie
best-seller
New

Toby Black | Fisherman Beanie

$87.00

Unit price
per 

4 colors, 1 size
  • OS
Toby Brown | Fisherman Beanie
best-seller
New

Toby Brown | Fisherman Beanie

5.0 (3)

$87.00

Unit price
per 

4 colors, 1 size
  • OS
Anderson Olive wide brim fedora hat on white background, angled view
Back view of woman in romper walking with Anderson Olive fedora and backpack
best-seller
New

Anderson Olive | Green Packable Wide Brim Fedora

4.9 (34)

$205.00

Unit price
per 

4 colors, 5 sizes
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  • M
  • L
  • XL
  • XXL
Anderson Brown wide brim fedora hat on white background, angled view
Woman standing in open field with Anderson Brown hat and linen outfit
best-seller
New

Anderson Brown | Packable Wide Brim Fedora Hat

4.9 (27)

$205.00

Unit price
per 

4 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear off white chunky knit beanie with pom pom, displayed on neutral background
Sold out

Willow Cream | Off White Beanie Chunky Knit

5.0 (6)

$87.00

Unit price
per 

2 colors, 1 size
  • OS
Will & Bear Chunky Brown Beanie made from 100% wool, displayed on neutral background
Camping adventure featuring Will & Bear Chunky Brown Beanie 100% wool, perfect for outdoor explorers
best-seller

Willow Brown | Chunky Brown Beanie 100% Wool

4.7 (6)

$87.00

Unit price
per 

2 colors, 1 size
  • OS
Buck Smoke | Black Felt Cowboy Hat
Men sitting on the edge of a truck wearing the Will & Bear Buck Smoke black felt cowboy hat, styled for rugged outdoor comfort.
best-seller
New

Buck Smoke | Black Felt Cowboy Hat

4.9 (47)

$234.00

Unit price
per 

4 colors, 4 sizes
  • S
  • M
  • L
  • XL
Buck Brown | Brown Felt Cowboy Hat
best-seller
New

Buck Brown | Brown Felt Cowboy Hat

5.0 (8)

$234.00

Unit price
per 

4 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Toby Mustard | Fisherman Beanie
New

Toby Mustard | Fisherman Beanie

5.0 (3)

$87.00

Unit price
per 

4 colors, 1 size
  • OS
Toby Cream | Fisherman Beanie
New

Toby Cream | Fisherman Beanie

4.5 (2)

$87.00

Unit price
per 

4 colors, 1 size
  • OS
Will & Bear Teddy Chestnut Wool UGG Bucket Hat crafted from premium wool and shearling, shown on neutral background
Top view of Will & Bear Teddy Chestnut Wool UGG Bucket Hat highlighting soft suede outer and wool lining
best-seller

Teddy Chestnut | Wool UGG Bucket Hat

4.9 (51)

$197.00

Unit price
per 

3 colors, 4 sizes
  • S
  • M
  • L
  • XL
Will & Bear Wide Brim Country Hat in olive green on neutral background, showcasing structured wool felt and flat brim.
Top-down view of Will & Bear Wide Brim Country Hat highlighting teardrop crown shape and structured finish.
best-seller
New

Explorer Olive | Wide Brim Country Hat

4.7 (61)

$234.00

Unit price
per 

2 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Flat lay of the Levi Dark Brown beanie made from wool, displayed on a neutral background
Person wearing the Levi Dark Brown beanie holding a vintage camera in a desert setting
Sold out

Levi Dark Brown | Winter Beanie

4.8 (313)

$87.00

Unit price
per 

4 colors, 1 size
  • OS
Will & Bear Levi Olive Brown Winter Beanie made from Australian wool, displayed on neutral background
Adventurous couple wearing Will & Bear Winter Beanies, exploring outdoors in cold climates
best-seller

Levi Olive Brown | Winter Beanie

4.8 (313)

$87.00

Unit price
per 

4 colors, 1 size
  • OS

Make it a winter to remember

A Will & Bear winter hat is the ultimate companion for cold weather, offering both warmth and style. Each winter hat is crafted from premium, sustainable materials designed to keep you cozy throughout the colder months. Our winter hats are unisex and timeless, making them a versatile addition to any wardrobe. From our iconic UGG bucket hat, Teddy, to our snug beanies, we're sure there's an option perfect for you.

When you choose a Will & Bear Winter Hat, you're supporting a brand committed to environmental sustainability. For every Winter Hat sold, we plant a native tree and donate 40% of our profits to support Australian farmers. So, your Winter Hat isn’t just about staying warm—it’s a meaningful contribution to a greener future. Be sure to check out our Men's Beanie collection and Stay warm through every adventure with Women's Beanie collection.