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

Mens Vacation Hats

Discover rugged men's holiday hats built for adventure.

11 Results

Calloway Fawn | Felt Fedora Hat
best-seller

Calloway Fawn | Felt Fedora Hat

4.9 (1842)

$119.00

Unit price
per 

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

Calloway Ash | Wide Brim Felt Fedora

4.9 (1842)

$119.00

Unit price
per 

5 colors, 5 sizes
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  • M
  • L
  • XL
  • XXL
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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  • M
  • L
  • XL
River Sand | Men’s & Women’s Straw Hat
best-seller

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

4.8 (127)

$102.00

Unit price
per 

4 sizes
  • S
  • M
  • L
  • XL

Andy Auburn | Dark Brown Country Hat

4.8 (569)

$127.00

Unit price
per 

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

Calloway Tan | Brown Widebrim Fedora

5.0 (96)

$119.00

Unit price
per 

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

Austin Sand | Straw Sun Hat

4.8 (23)

$119.00

Unit price
per 

2 colors, 4 sizes
  • S
  • M
  • L
  • XL
Sunny Sand | Crushable Straw Bucket Hat
Sold out

Sunny Sand | Crushable Straw Bucket Hat

4.8 (33)

$102.00

Unit price
per 

2 colors, 3 sizes
  • S
  • M
  • L

Austin Brown | Brown Straw Wide Brim Hat

4.8 (23)

$119.00

Unit price
per 

2 colors, 4 sizes
  • S
  • M
  • L
  • XL
Rustic wide brim straw hat Jude Sand by Will & Bear
Top view of rustic wide brim straw hat Jude Sand by Will & Bear
New

Jude Sand | Wide Brim Raffia Straw Hat

3.0 (1)

$85.00

Unit price
per 

4 sizes
  • S
  • M
  • L
  • XL

Welcome to our collection of Men's Holiday Hats, your go-to source for headwear that combines comfort, durability, and functionality for all your sunny adventures.

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

Crafted with rugged durability, these 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 our holiday hats 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.