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Man standing with his girlfriend at the beach while wearing a vacation or holiday hat by Will & Bear

Men's Holiday Hat

Discover rugged men's holiday hats built for adventure.

19 Results

Teddy Brown | Wool UGG Bucket Hat
New

Teddy Brown | Wool UGG Bucket Hat

4.9 (33)

¥16,900

Unit price
per 

3 colors, 4 sizes
  • S
  • M
  • L
  • XL
Teddy Fawn | Wool UGG Bucket Hat
New

Teddy Fawn | Wool UGG Bucket Hat

4.9 (33)

¥16,900

Unit price
per 

3 colors, 4 sizes
  • S
  • M
  • L
  • 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.
New

Buck Cream | White Cowboy Hat Felt

¥15,000

Unit price
per 

3 colors, 4 sizes
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  • L
  • XL
A Will & Bear removable string bucket hat in chocolate brown, displayed on a neutral background.
A couple wearing Will & Bear removable string bucket hats at the beach, enjoying the coastal view.
New

Billie Brown | Removable String Bucket Hat

4.8 (4)

¥8,400

Unit price
per 

2 colors, 4 sizes
  • S
  • M
  • L
  • XL
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 (1868)

¥13,100

Unit price
per 

5 colors, 5 sizes
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  • M
  • L
  • XL
  • XXL
Will & Bear Andy Oak Brown Wide Brim Fedora made from sustainable wool, displayed on neutral background
Top view of Will & Bear Andy Oak Brown Wide Brim Fedora, lightweight and crushable design
best-seller

Andy Oak | Brown Wide Brim Fedora

4.8 (576)

¥14,100

Unit price
per 

3 colors, 4 sizes
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  • M
  • L
  • XL
Ranger Milo | Vintage Corduroy Cap
New

Ranger Milo | Vintage Corduroy Cap

5.0 (1)

¥4,700

Unit price
per 

3 colors, 1 size
  • OS

Calloway Ash | Wide Brim Felt Fedora

4.9 (1868)

¥13,100

Unit price
per 

5 colors, 5 sizes
  • S
  • M
  • L
  • XL
  • XXL
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 (130)

¥11,300

Unit price
per 

4 sizes
  • S
  • M
  • L
  • XL

Andy Auburn | Dark Brown Country Hat

4.8 (576)

¥14,100

Unit price
per 

3 colors, 4 sizes
  • S
  • M
  • L
  • 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
best-seller
New

Calloway Tan | Brown Widebrim Fedora

5.0 (99)

¥13,100

Unit price
per 

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

Baker Tan | Brown Cord Bakerboy Cap

4.9 (155)

¥7,500

Unit price
per 

2 colors, 3 sizes
  • S
  • M
  • L
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)

¥12,200

Unit price
per 

4 sizes
  • S
  • M
  • L
  • XL

Foster Green | Green Fiddler Cap

4.9 (154)

¥6,500

Unit price
per 

2 colors, 3 sizes
  • S
  • M
  • L

Austin Sand | Straw Sun Hat

4.8 (28)

¥13,100

Unit price
per 

2 colors, 4 sizes
  • S
  • M
  • L
  • XL

Austin Brown | Brown Straw Wide Brim Hat

4.8 (28)

¥13,100

Unit price
per 

2 colors, 4 sizes
  • S
  • M
  • L
  • XL
Will & Bear Brown 5 Panel Cap made from organic cotton, displayed on neutral background
Front view of Will & Bear Brown 5 Panel Cap showing minimalist design and sustainable craftsmanship
Sold out

Archie Walnut | Brown 5 Panel Cap

4.2 (6)

¥4,700

Unit price
per 

1 color

Hat Carry Clips

4.6 (168)

¥1,900

Unit price
per 

Will & Bear removable string bucket hat in natural off-white, crafted from breathable cotton with adjustable chin strap.
Couple wearing Will & Bear removable string bucket hats on the beach, perfect for sun protection and surfside adventures.
New

Billie Bone | Removable String Bucket Hat

5.0 (2)

¥8,400

Unit price
per 

2 colors, 4 sizes
  • S
  • M
  • L
  • XL

Why Buy a Men's Holiday Hat from Will & Bear?

Whether you're spending the day on a sandy beach, hiking scenic trails, or simply lounging by the pool, our men's holiday hat offers the reliable shade you need to keep cool and protected.

Crafted with rugged durability, our men's holiday hats are built to last, ensuring they can withstand the elements and stand by you through countless holidays and outdoor escapades.

Imagine spending your days free from the sun’s harsh glare, thanks to the hat that feels just as adventurous as you do.

What sets men's holiday hat apart is the use of breathable materials that keep your head cool, no matter how high the temperatures soar. These aren't just ordinary hats; they're a tradition passed down from sun-loving, adventure-seeking folks who know just how important the right hat can be.

Whether you're exploring new destinations or enjoying a staycation, our hats offer a laid-back and practical solution to sun protection.

Dive in to discover the perfect companion for your next holiday, and enjoy every sunny moment with peace of mind and comfort. And for even more styles to suit your getaway, explore our full collection of holiday hats.

Men's Holiday Hat FAQs

Enjoy FREE shipping on orders above $150. 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 Australian states, ensuring that your hat arrives in 3-5 business days depending on your location.

For international orders, delivery times vary based on the destination and usually take between 7-14 business days. You’ll receive a tracking number once your order is dispatched so you can monitor its progress.

Explore Our Range of Men's Holiday Hats

Discover our carefully curated collection of men's holiday hats, designed to elevate your style and provide essential sun protection on your travels. From classic fedoras to versatile wide-brim styles, each men's holiday hats is crafted with sustainable materials and thoughtful design, ensuring you stay comfortable and chic on your next adventure. Whether you're lounging on a tropical beach or exploring a vibrant city, our men's holiday hats are the perfect accessory to complement your holiday wardrobe. Experience the perfect blend of function and fashion with Will & Bear's exceptional range of men's holiday hats.