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A man and woman on vacation wearing wide brims hats by Will & Bear, in a rustic bohemian pool setting.

Holiday Hats

Discover unbeatable comfort in our sustainably crafted holiday hat—designed for life’s every adventure.

18 Results

Billie Brown | Removable String Bucket Hat
Couple wearing string bucket hats near the beach
New

Billie Brown | Removable String Bucket Hat

4.8 (4)

$76.00

Unit price
per 

4 sizes
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Andy Oak | Brown Wide Brim Fedora
best-seller

Andy Oak | Brown Wide Brim Fedora

4.8 (569)

$127.00

Unit price
per 

3 colors, 4 sizes
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  • XL

Austin Brown | Brown Straw Wide Brim Hat

4.8 (27)

$119.00

Unit price
per 

3 colors, 4 sizes
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  • XL
Calloway Tan | Brown Widebrim Fedora
best-seller

Calloway Tan | Brown Widebrim Fedora

5.0 (97)

$119.00

Unit price
per 

5 colors, 5 sizes
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  • M
  • L
  • XL
  • XXL

Stevie Sand | Raffia Straw Bucket

5.0 (45)

$102.00

Unit price
per 

3 sizes
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  • L

Austin Sand | Straw Sun Hat

4.8 (27)

$119.00

Unit price
per 

3 colors, 4 sizes
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  • M
  • L
  • XL
River Sand | Men’s & Women’s Straw Hat
best-seller

River Sand | Men’s & Women’s Straw Hat

4.8 (129)

$102.00

Unit price
per 

4 sizes
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  • M
  • L
  • XL

Buck Bone | White Straw Cowboy Hat

4.6 (9)

$110.00

Unit price
per 

4 sizes
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  • L
  • XL

Calloway Cream | White Felt Sun Hat

4.9 (1847)

$119.00

Unit price
per 

5 colors, 4 sizes
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  • M
  • L
  • XL
Rider Bone | White Palm Straw Hat
best-seller

Rider Bone | White Palm Straw Hat

4.7 (93)

$110.00

Unit price
per 

4 sizes
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  • L
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Andy Cream | White Felt Sun Hat
best-seller

Andy Cream | White Felt Sun Hat

4.8 (569)

$127.00

Unit price
per 

3 colors, 4 sizes
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  • M
  • L
  • XL
Calloway Fawn | Felt Fedora Hat
best-seller

Calloway Fawn | Felt Fedora Hat

4.9 (1847)

$119.00

Unit price
per 

5 colors, 5 sizes
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  • XL
  • XXL
Front studio shot of recycled hemp bucket hat Bodhi Carob
Top down studio shot of recycled hemp bucket hat Bodhi Carob
New

Camp Bodhi Carob | Recycled Hemp Bucket Hat

4.9 (11)

$85.00

Unit price
per 

2 colors, 3 sizes
  • S
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William cream white packable travel hat front view
William cream white packable travel hat top view
New

William Cream | Crushable Travel Hat | White Felt Fedora Hat

4.6 (7)

$110.00

Unit price
per 

4 colors, 4 sizes
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  • XL
William Oak soft wool wide-brim fedora front
William Oak soft wool wide-brim fedora top
best-seller

William Oak | Crushable Travel Hat

4.9 (1445)

$110.00

Unit price
per 

4 colors, 5 sizes
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  • L
  • XL
  • XXL
Sunny Husk | Women’s Straw Bucket Hat
best-seller

Sunny Husk | Women’s Straw Bucket Hat

4.8 (35)

$102.00

Unit price
per 

2 colors, 3 sizes
  • S
  • M
  • L
Sunny Sand | Crushable Straw Bucket Hat
Sold out

Sunny Sand | Crushable Straw Bucket Hat

4.8 (35)

$102.00

Unit price
per 

2 colors, 3 sizes
  • S
  • M
  • L

Baker Fawn | White Cord Newsboy Cap

4.9 (151)

$68.00

Unit price
per 

2 colors, 3 sizes
  • S
  • L
  • M

Why Buy a Will & Bear Holiday Hat?

A Will & Bear holiday hat isn't just for show; they're your trusty companion for sunny adventures and lazy beach days. Crafted with sun protection in mind, our holiday hats are perfect for shielding you from those harsh rays while adding a touch of holiday flair to any outfit. Whether you're exploring a new city, lounging by the pool, or heading out on a casual stroll, you'll find our hats to be as reliable as an old friend, always ready to keep you comfortable and protected.

What truly sets our holiday hats apart is their lightweight comfort and durable construction. Designed for all-day wearability, these hats are perfect for everything from backyard barbecues to hikes in the great outdoors. You'll appreciate the thoughtful design that ensures they remain a staple in your wardrobe season after season.

And let's not forget the rich tradition behind these versatile pieces—they're a nod to holiday celebrations around the world, capturing the spirit of relaxation and joy. Choose from our men’s holiday hats and women’s holiday hats, each crafted to reflect the timeless essence of the season.

Holiday Hats FAQs

Enjoy FREE shipping on orders above $110 USD. At Will & Bear, we pride ourselves on quick delivery! Your hat ships fast, typically within 48 hours of placing your order. We ship to all US states, ensuring that your hat arrives in 3-8 business days depending on your location.You’ll receive a tracking number once your order is dispatched so you can monitor its progress.