Your cart

Your cart is empty

Check out these collections.

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

26 Results

Andy Auburn | Dark Brown Country Hat

4.8 (586)

$120.00

Unit price
per 

3 colors, 4 sizes
  • S
  • M
  • L
  • XL
Will & Bear Brown Country Hat crafted from sustainable wool, displayed on neutral background
Top view of Will & Bear Brown Country Hat, showcasing classic wide brim and teardrop crown
best-seller
New

Explorer Taupe | Brown Country Hat

4.7 (51)

$128.00

Unit price
per 

2 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear Calloway Tan Brown Wide Brim Fedora made from 100% wool, displayed on neutral background
Top view of Will & Bear Calloway Tan Brown Wide Brim Fedora highlighting classic shape and leather band
Sold out

Calloway Tan | Brown Widebrim Fedora

5.0 (101)

$112.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear Calloway Fawn Felt Fedora Hat made from premium wool, displayed on neutral background
Top view of Will & Bear Calloway Fawn Felt Fedora Hat, showcasing structured crown and leather band
best-seller

Calloway Fawn | Felt Fedora Hat

4.9 (1888)

$112.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
  • S
  • M
  • L
  • XL
  • XXL

Calloway Ash | Wide Brim Felt Fedora

4.9 (1888)

$112.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear Calloway Black wide brim hat made from premium wool, photographed on a neutral backdrop.
Overhead view of the Will & Bear Calloway Black wide brim hat showing crown shape and symmetry.
best-seller

Calloway Black | Black Wide Brim Hat

4.9 (1888)

$112.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear Crushable Travel Hat in dark brown, made from soft felt and designed for packability, shown on neutral background
Top view of Will & Bear Crushable Travel Hat showing teardrop crown and wide brim, crafted for easy packing
best-seller

William Brown | Crushable Travel Hat

4.9 (1523)

$104.00

Unit price
per 

4 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear William Oak light brown crushable travel hat made from sustainable wool with classic fedora shape.
Top view of Will & Bear William Oak wool felt fedora hat – wide brim, light brown tone, travel-ready design.
best-seller

William Oak | Crushable Travel Hat

4.9 (1523)

$104.00

Unit price
per 

4 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
Will & Bear William Cream crushable travel hat – white felt fedora hat made from natural wool with classic wide brim.
Top view of Will & Bear William Cream white felt fedora hat – structured crown with crushable design ideal for travel.
New

William Cream | Crushable Travel Hat | White Felt Fedora Hat

4.7 (11)

$104.00

Unit price
per 

4 colors, 4 sizes
  • S
  • M
  • L
  • XL
Will & Bear Doc Black Wool Fisherman’s Beanie on neutral background, showcasing ribbed knit design and deep black tone.
Straight-on view of the Will & Bear Doc Black Wool Fisherman’s Beanie showing shape and cuff detail on neutral background.
Sold out

Doc Black | Wool Fishermans Beanie

4.9 (78)

$44.00

Unit price
per 

1 color, 1 size
  • One Size

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.