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A couple in all-season wool hats by Will & Bear explore white cliffs together.

Men's All Season Hats

Discover men's all season hats for year-round comfort.

32 Results

Duke Straw | Raffia Cowboy Hat
Two people wearing cowboy hats against a clear blue sky.
15% off
best-seller
New

Duke Straw | Raffia Cowboy Hat

5.0 (3)

Regular price $128.00 $109.00

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4 sizes
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Buck Brown | Brown Felt Cowboy Hat
25% off
best-seller
New

Buck Brown | Brown Felt Cowboy Hat

5.0 (5)

Regular price $128.00 $96.00

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per 

4 colors, 5 sizes
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  • XXL
Buck Oak | Light Brown Felt Cowboy Hat
Woman wearing Woman enjoying golden hour on a porch wearing the Will & Bear Buck Oak brown felt cowboy hat, styled for relaxed country living.
25% off
New

Buck Oak | Light Brown Felt Cowboy Hat

4.9 (39)

Regular price $128.00 $96.00

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per 

4 colors, 4 sizes
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Calloway Dark Brown wide brim fedora hat on white background, angled side view
Couple by 4WD at sunset with surfboard, wearing Calloway Dark Brown hats
30% off
New

Calloway Brown | Wide-brim Fedora Hat

5.0 (3)

Regular price $112.00 $78.00

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per 

6 colors, 5 sizes
  • +1 more
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Anderson Brown wide brim fedora hat on white background, angled view
Woman standing in open field with Anderson Brown hat and linen outfit
15% off
best-seller
New

Anderson Brown | Packable Wide Brim Fedora Hat

5.0 (17)

Regular price $112.00 $95.00

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per 

5 colors, 5 sizes
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Anderson Olive wide brim fedora hat on white background, angled view
Back view of woman in romper walking with Anderson Olive fedora and backpack
15% off
best-seller
New

Anderson Olive | Green Packable Wide Brim Fedora

4.9 (23)

Regular price $112.00 $95.00

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per 

5 colors, 5 sizes
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  • 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

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per 

4 colors, 4 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 $104.00 $88.00

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per 

4 colors, 5 sizes
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  • XXL
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.
25% off
best-seller
New

Buck Smoke | Black Felt Cowboy Hat

4.9 (39)

Regular price $128.00 $96.00

Unit price
per 

4 colors, 4 sizes
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  • XL
Will & Bear white cowboy hat made from premium felt, displayed on a neutral background to show its structured shape and wide brim.
Couple walking through the outback wearing Will & Bear white cowboy hats made from Australian wool felt.
25% off
New

Buck Cream | White Cowboy Hat Felt

5.0 (2)

Regular price $128.00 $96.00

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per 

4 colors, 4 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
21% off
best-seller

Calloway Fawn | Felt Fedora Hat

4.9 (1888)

Regular price $112.00 $89.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
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  • XXL
Will & Bear Calloway Cream white sun felt hat with wide brim, crafted from sustainable wool, shown on a neutral backdrop.
Woman wearing the Will & Bear Calloway Cream white sun felt hat by the ocean, enjoying a coastal sunset.
21% off

Calloway Cream | Felt Sun Hat

4.9 (1888)

Regular price $112.00 $89.00

Unit price
per 

6 colors, 4 sizes
  • +1 more
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Anderson Cream wide brim fedora hat on white background, angled view
Woman seated in open landscape wearing Anderson Cream hat and linen jumpsuit
15% off
best-seller
New

Anderson Almond | Cream Packable Wide Brim Fedora Hat

5.0 (23)

Regular price $112.00 $95.00

Unit price
per 

5 colors, 4 sizes
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Will & Bear Anderson Navy Soft Felt Fedora with classic teardrop crown and wide brim for everyday adventure
Top view of Will & Bear Anderson Navy Soft Felt Fedora highlighting the smooth felt finish and structured crown
Sold out

Anderson Navy | Soft Felt Fedora

4.9 (441)

$112.00

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per 

5 colors, 4 sizes
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  • XL
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 $112.00 $78.00

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per 

6 colors, 5 sizes
  • +1 more
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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 $112.00 $78.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
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  • 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.
30% off

Calloway Black | Black Wide Brim Hat

4.9 (1888)

Regular price $112.00 $78.00

Unit price
per 

6 colors, 5 sizes
  • +1 more
  • S
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  • XL
  • XXL
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 $104.00 $83.00

Unit price
per 

4 colors, 5 sizes
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  • L
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  • XXL
Will & Bear Andy Auburn Dark Brown Country Hat featuring a structured teardrop crown and wide brim for outdoor adventures
Female explorer wearing Will & Bear Andy Auburn Dark Brown Country Hat indoors, perfect for everyday style and travel
Sold out

Andy Auburn | Dark Brown Country Hat

4.8 (589)

Regular price $120.00 $84.00

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per 

3 colors, 4 sizes
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Will & Bear Andy Oak Brown Wide Brim Fedora made from sustainable wool, displayed on neutral background
Woman adjusting Will & Bear Brown Wide Brim Fedora outdoors, perfect for travel and adventure
30% off
best-seller

Andy Oak | Brown Wide Brim Fedora

4.8 (589)

Regular price $120.00 $84.00

Unit price
per 

3 colors, 4 sizes
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  • XL
Will & Bear White Felt Sun Hat with wide brim, crafted for sustainable outdoor adventures
Outdoor moment with Will & Bear White Felt Sun Hat, designed for rugged landscapes and sun coverage
30% off
best-seller

Andy Cream | White Felt Sun Hat

4.8 (589)

Regular price $120.00 $84.00

Unit price
per 

3 colors, 4 sizes
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  • M
  • L
  • XL
Will & Bear Brown Straw Wide Brim Hat 
 Austin Brown made from natural palm fibre with chin strap, shown on neutral background
Man in relaxed coastal setting wearing Will & Bear Brown Straw Wide Brim Hat for sun protection and style
30% off

Austin Brown | Brown Straw Wide Brim Hat

4.9 (40)

Regular price $112.00 $78.00

Unit price
per 

2 colors, 4 sizes
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  • M
  • L
  • XL
Will & Bear straw sun hat on neutral background, featuring wide brim and chin strap for sun protection and adventure-ready style
Woman wearing Will & Bear straw sun hat sitting with surfboard on sandy beach at sunset
21% off

Austin Sand | Straw Sun Hat

4.9 (40)

Regular price $112.00 $89.00

Unit price
per 

2 colors, 4 sizes
  • S
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  • L
  • XL

Why Buy a Will & Bear Men's All Season Hat?

Explore our Men's All Season Hats collection, where practicality meets tradition. Whether you’re hiking through mountain trails, enjoying a sunny afternoon in the park, or simply tackling a day of errands, these hats are crafted to cover you—literally and figuratively—in all sorts of weather.

Made with durable materials, these hats are designed to stand the test of time, delivering long-lasting protection from harsh sun rays and unexpected showers. Comfort is never out of season, and these hats promise to keep you feeling great no matter what the weather throws your way.

Our collection pays homage to classic hat silhouettes, celebrating timeless styles that have been appreciated for generations. Each hat serves as a dependable companion, offering year-round comfort without compromising style or functionality.

The charm of these hats is the seamless blend of traditional designs with modern necessity. Versatile and reliable, our hats are perfect for everyday adventures or just a laid-back day out. Enjoy a piece of tradition on every outing, knowing that your hat is ready to handle whatever the day has in store.

Men's All Season Hats FAQs

Explore Our Range of Men's All Season Hats

Discover the versatility and style of our men's all season hats, crafted to provide comfort and complement any outfit throughout the year. Designed with high-quality materials, Will & Bear men's all season hats offer durability and protection, whether you're shielding yourself from the summer sun or braving a light winter chill. Our collection features a variety of classic and contemporary styles, ensuring that there is a perfect fit for every occasion. At Will & Bear, we believe in merging fashion with function, so explore our selection and find the perfect hat to express your individuality and embrace the outdoors.