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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

22 Results

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)

Regular price ¥16,100 ¥11,300

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6 colors, 5 sizes
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Will & Bear Calloway Fawn Felt Fedora Hat made from premium wool, displayed on neutral background
Woman adventuring outdoors in Will & Bear Felt Fedora Hat, crafted for travel and exploration
20% off
best-seller

Calloway Fawn | Felt Fedora Hat

4.9 (1888)

Regular price ¥16,100 ¥12,900

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6 colors, 5 sizes
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Will & Bear Calloway Ash wide brim felt fedora hat shown on a neutral background.
Woman wearing the Will & Bear Calloway Ash wide brim felt fedora while gazing into the distance in a golden field.
30% off

Calloway Ash | Wide Brim Felt Fedora

4.9 (1888)

Regular price ¥16,100 ¥11,300

Unit price
per 

6 colors, 5 sizes
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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.
30% off

Calloway Black | Black Wide Brim Hat

4.9 (1888)

Regular price ¥16,100 ¥11,300

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6 colors, 5 sizes
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Will & Bear Crushable Travel Hat in dark brown, made from soft felt and designed for packability, shown on neutral background
Man on a road trip wearing Will & Bear Crushable Travel Hat, perfect for flexible travel and sun protection
20% off
best-seller

William Brown | Crushable Travel Hat

4.9 (1527)

Regular price ¥14,900 ¥11,900

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4 colors, 5 sizes
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Will & Bear William Oak light brown crushable travel hat made from sustainable wool with classic fedora shape.
Couple standing together wearing Will & Bear hats – woman in William Cream, man in William Oak light brown crushable travel hat.
15% off
best-seller

William Oak | Crushable Travel Hat

4.9 (1527)

Regular price ¥14,900 ¥12,700

Unit price
per 

4 colors, 5 sizes
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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.