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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.

41 Results

Austin Sand | Straw Sun Hat

4.9 (40)

$144.00

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2 colors, 4 sizes
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Will & Bear Rider Bone White Palm Straw Hat crafted for sun protection and outdoor adventures, displayed on neutral background
Top view of Will & Bear Rider Bone White Palm Straw Hat featuring wide brim and leather chin strap
best-seller

Rider Bone | White Palm Straw Hat

4.7 (94)

$133.00

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4 sizes
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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 (1887)

$144.00

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6 colors, 5 sizes
  • +1 more
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  • XXL

Calloway Cream | Felt Sun Hat

4.9 (1887)

$144.00

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per 

6 colors, 4 sizes
  • +1 more
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Will & Bear Wide-brim Bucket Hat in off-white, lightweight and breathable for sun protection
Top view of Will & Bear Wide-brim Bucket Hat showcasing wide brim and adjustable chin strap
best-seller

Bodhi Bone | Wide-brim Bucket Hat

4.9 (15)

$92.00

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per 

1 color, 4 sizes
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Will & Bear River Sand Men's and Women's Straw Hat made from handwoven palm, shown on neutral background
Top view of Will & Bear River Sand Men's and Women's Straw Hat with natural wide brim and pinch crown
best-seller

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

4.8 (132)

$123.00

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per 

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
best-seller

Andy Oak | Brown Wide Brim Fedora

4.8 (583)

$154.00

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per 

3 colors, 4 sizes
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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
best-seller

Andy Cream | White Felt Sun Hat

4.8 (583)

$154.00

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per 

3 colors, 4 sizes
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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.
Sold out

William Cream | Crushable Travel Hat | White Felt Fedora Hat

4.7 (11)

$133.00

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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.
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 (1519)

$133.00

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per 

4 colors, 5 sizes
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Baker Fawn | White Cord Newsboy Cap

4.9 (157)

$82.00

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per 

2 colors, 3 sizes
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  • M
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 (306)

$61.00

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per 

6 colors, 1 size
  • +1 more
  • OS
Will & Bear Yellow Vintage Dad Cap – Riley Gold – angled front view featuring embroidered "More Trees" detail on organic cotton, displayed on a neutral background.
Will & Bear Yellow Vintage Dad Cap – Riley Gold – full front view showcasing classic shape and minimalist design, displayed on a neutral background.
Sold out

Riley Gold | Womens Dad Cap

5.0 (3)

$51.00

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2 colors
Will & Bear White Vintage Dad Cap – Riley Bone – side angle view showing embroidered "More Trees" slogan on natural cotton, displayed on a neutral background.
Will & Bear White Vintage Dad Cap – Riley Bone – direct front view highlighting clean shape and slogan detail, displayed on a neutral background.
Sold out

Riley Bone | White Vintage Dad Cap

5.0 (3)

$51.00

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per 

2 colors
Side View of Will & Bear Ranger Brown Vintage 5-Panel Cap on Neutral Background – Organic Cotton Cap with Flat Brim and Embroidered Logo.
best-seller

Ranger Brown | Vintage 5-panel cap

4.0 (9)

$51.00

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per 

3 colors, 1 size
  • OS
Front View of Will & Bear Ranger Milo Vintage Corduroy Cap on Neutral Background – Two-Tone Panel Cap with Embroidered Patch.
Woman Wearing Will & Bear Ranger Milo Vintage Corduroy Cap on the Beach – Lightweight Summer Cap.
New

Ranger Milo | Vintage Corduroy Cap

5.0 (2)

$51.00

Unit price
per 

3 colors, 1 size
  • OS
Will & Bear Brown 5 Panel Cap made from organic cotton, displayed on neutral background
best-seller
New

Archie Walnut | Brown 5 Panel Cap

4.0 (7)

$51.00

Unit price
per 

2 colors

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

Explore Our Range of Holiday Hats

Discover the perfect vacation hat and holiday hat with Will & Bear, where style meets sustainability. Our collection offers a variety of designs to complement any festive occasion, from classic wide-brimmed sun hats to cozy knitted beanies. Each holiday hat is crafted from high-quality, eco-friendly materials, ensuring that you not only look good but also feel good about your choice. Whether you’re lounging by the beach or strolling through a winter wonderland, our holiday hats provide both protection and flair. Celebrate the season in style with timeless pieces that embody our commitment to the environment and exceptional craftsmanship.