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Vacation Hats – Stylish Sun Hats for Every Getaway

  • Sedona XL Fedora for Large Head by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Sedona XL Fedora for Large Head by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Sedona XL Fedora for Large Head by Wallaroo Hat Company

    $ 61.00

    The Sedona Safari Hat XL by Wallaroo Hat Company brings one of Wallaroo's most popular sun hats to men and women who need a little extra room. Desi...

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    $ 61.00
  • Charlie XL Fedora for Large Heads by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Charlie XL Fedora for Large Heads by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Charlie XL Fedora for Large Heads by Wallaroo Hat Company

    $ 61.00

    The Charlie XL Fedora by Wallaroo Hat Company brings the brand's best-selling fedora design to women and men with larger head sizes seeking a comfo...

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    $ 61.00
  • Wide Brim Straw Ponytail Facesaver Sun Hat - Jeanne Simmons Wide Brim Hat Jeanne Simmons Accessories
    Wide Brim Straw Ponytail Facesaver Sun Hat - Jeanne Simmons Wide Brim Hat Jeanne Simmons Accessories JS8301-BLK Black Tweed OS

    Wide Brim Straw Ponytail Facesaver Sun Hat - Jeanne Simmons

    $ 35.00

    Stay cool, protected, and effortlessly stylish with the Wide Brim Straw Ponytail Facesaver Sun Hat from Jeanne Simmons Accessories. Designed for ac...

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    $ 35.00
  • Adjustable Size Hat for Ponytails - Boardwalk Style Facesaver Hat Boardwalk Style Hats
    Adjustable Size Hat for Ponytails - Boardwalk Style Facesaver Hat Boardwalk Style Hats DA1367-BLK Brown Tweed OS

    Adjustable Size Hat for Ponytails - Boardwalk Style

    $ 37.50

    Enjoy sun-smart style and a perfect fit with this adjustable ponytail sun hat, thoughtfully designed for larger head sizes. The elastic strap closu...

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    $ 37.50
  • Cooling Dimensional Brim Hiking Hat, Chin Strap - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Cooling Dimensional Brim Hiking Hat, Chin Strap - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC416-KAKI2 Khaki Labeled: S/M; Actual size: 55.5 cm (S)
    Sale

    Cooling Dimensional Brim Hiking Hat, Chin Strap - DPC Outdoor Headwear

    Original Price $ 40.00
    Current Price $ 20.00

    Take on hot, sunny days with confidence in this nylon blend camp hat featuring advanced HyperKewl™ cooling technology. Designed for high-performanc...

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    Original Price $ 40.00
    Current Price $ 20.00
    Sale
  • Striped Crocheted Toyo Summer Hat - Sun 'N' Sand Hats Cloche Sun N Sand Hats
    Striped Crocheted Toyo Summer Hat - Sun 'N' Sand Hats Cloche Sun N Sand Hats HH3647 Tan ML (58 cm)

    Striped Crocheted Toyo Summer Hat - Sun 'N' Sand Hats

    $ 52.00

    Elevate your warm-weather style with the Striped Crocheted Toyo Summer Hat from Sun ’N’ Sand. Expertly crafted from finely crocheted premium toyo s...

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    $ 52.00
  • Flex Weave Straw Pinched Crown Fedora Hat - Boardwalk Style Fedora Hat Boardwalk Style Hats DA1352-BLK Black Heather OS (57 cm)
    Flex Weave Straw Pinched Crown Fedora Hat - Boardwalk Style Fedora Hat Boardwalk Style Hats

    Flex Weave Straw Pinched Crown Fedora Hat - Boardwalk Style

    $ 43.00

    Refined yet practical, this pinched crown fedora hat is crafted from premium Flex-Weave straw for lightweight durability and elevated summer style....

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    $ 43.00
  • Flex Weave Straw Pinched Crown Safari Hat - Boardwalk Style Safari Hat Boardwalk Style Hats DA1353-TAUP Taupe OS (57 cm)
    Flex Weave Straw Pinched Crown Safari Hat - Boardwalk Style Safari Hat Boardwalk Style Hats

    Flex Weave Straw Pinched Crown Safari Hat - Boardwalk Style

    $ 45.00

    Elevate your warm-weather wardrobe with this pinched crown sun hat, crafted from premium Flex-Weave straw for a refined look that travels beautiful...

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    $ 45.00
  • Flex Weave Straw Flat Top Bucket Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Flex Weave Straw Flat Top Bucket Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA1356-TAUP Taupe OS (57 cm)

    Flex Weave Straw Flat Top Bucket Hat - Boardwalk Style

    $ 42.00

    Make a statement in the sun with this stunning flat-top bucket hat, designed with a dramatic 4.5-inch wide downward-sloping brim for exceptional co...

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    $ 42.00
  • Flex Weave Straw Lampshade Style Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA1355-NAT Natural Heather OS (57 cm)
    Flex Weave Straw Lampshade Style Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats

    Flex Weave Straw Lampshade Style Hat - Boardwalk Style

    $ 49.00

    Make a sophisticated statement in the sun with this lampshade-style hat, designed with a dramatic 5-inch wide downward-sloping brim for ultimate co...

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    $ 49.00
  • Flex Weave Straw Asymmetrical Brim Sun Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA1354-NAT Natural Heather OS (57 cm)
    Flex Weave Straw Asymmetrical Brim Sun Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats

    Flex Weave Straw Asymmetrical Brim Sun Hat - Boardwalk Style

    $ 50.00

    Elevate your sun style with this beautiful Flex-Weave straw hat, designed with a graceful dome crown and a striking asymmetrical brim for modern so...

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    $ 50.00
  • Flex Weave Straw Wide Brim Beach Hat - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats DA1350-NAT Natural Heather OS (57 cm)
    Flex Weave Straw Wide Brim Beach Hat - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats

    Flex Weave Straw Wide Brim Beach Hat - Boardwalk Style

    $ 49.00

    Turn every shoreline stroll into a style moment with this stunning Flex-Weave straw beach hat, designed to elevate your seaside and resort adventur...

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    $ 49.00
  • Wide Asymmetrical Brim Summer Hat with Bow - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Wide Asymmetrical Brim Summer Hat with Bow - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA1839-BLK Black tweed OS (57 cm)

    Wide Asymmetrical Brim Summer Hat with Bow - Boardwalk Style

    $ 34.00

    Step into summer with confidence in this striking asymmetrical sun hat that balances style with serious sun protection. The dramatic 5.5-inch front...

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    $ 34.00
  • Straw Beach Hat with Two-Tone Knot Band - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats
    Straw Beach Hat with Two-Tone Knot Band - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats DA1314-BLK Black OS (57 cm)

    Straw Beach Hat with Two-Tone Knot Band - Boardwalk Style

    $ 29.00

    Embrace effortless coastal elegance with this timeless straw beach hat, designed to elevate your seaside adventures. The graceful dome crown and ex...

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    $ 29.00
  • Washable Poly-Straw Facesaver Hat with Bow - Karen Keith Hats Facesaver Hat Great hats by Karen Keith PP23-C Tan OS (58 cm)
    Washable Poly-Straw Facesaver Hat with Bow - Karen Keith Hats Facesaver Hat Great hats by Karen Keith PP23-B Natural OS (58 cm)

    Washable Poly-Straw Facesaver Hat with Bow - Karen Keith Hats

    $ 30.00

    Protect your skin while staying active with this versatile poly-straw facesaver hat. Featuring UPF 50+ sun protection, it keeps harmful rays at bay...

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    $ 30.00
  • Straw Safari Hat with Pastel Tribal Band - Karen Keith Hats Safari Hat Great hats by Karen Keith N13-A Toast OS (57 cm)
    Straw Safari Hat with Pastel Tribal Band - Karen Keith Hats Safari Hat Great hats by Karen Keith N13-B White OS (57 cm)

    Straw Safari Hat with Pastel Tribal Band - Karen Keith Hats

    $ 30.00

    Step into the sun with unwavering confidence in this expertly crafted straw safari hat. Engineered with UPF 50+ protection and a sophisticated pape...

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    $ 30.00
  • Washable Poly-Straw Safari Hat, UPF50 - Karen Keith Hats Safari Hat Great hats by Karen Keith PP13-A Toast Tweed OS (57.5 cm)

    Washable Poly-Straw Safari Hat, UPF50 - Karen Keith Hats

    $ 30.00

    Own your outdoor story. This poly-straw safari hat empowers you to explore without limits, delivering robust UPF 50+ sun protection paired with was...

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    $ 30.00
  • Washable Poly-Straw Bucket Hat, UPF50 - Karen Keith Hats Cloche Great hats by Karen Keith PP15-A Toast Tweed OS (58 cm)
    Washable Poly-Straw Bucket Hat, UPF50 - Karen Keith Hats Cloche Great hats by Karen Keith PP15-B Ivory OS (58 cm)

    Washable Poly-Straw Bucket Hat, UPF50 - Karen Keith Hats

    $ 33.00

    This poly-straw bucket hat redefines sun protection for the modern adventurer. Engineered with UPF 50+ defense, it shields you from harmful rays wh...

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    $ 33.00
  • Extra Wide Elongated Brim Sun Hat - Sun 'N' Sand Hats Wide Brim Sun Hat Sun N Sand Hats HH3305 Brown OS (57 cm)

    Extra Wide Elongated Brim Sun Hat - Sun 'N' Sand Hats

    $ 46.00

    Elevate your beach style with this stunning wide-brim sun hat designed for the confident woman who refuses to compromise on protection or elegance....

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    $ 46.00

Vacation Hats for Every Adventure

The perfect vacation starts with the perfect hat. Whether you're relaxing on a tropical beach, exploring historic cities, enjoying a luxury cruise, or sightseeing in a new destination, our collection of Vacation Hats combines stylish designs with dependable sun protection for every journey.

Choose from wide-brim sun hats, packable straw hats, colorful bucket hats, breezy safari hats, stylish fedoras, sun visors, and lightweight travel hats designed for men and women. Many styles feature UPF 50+ sun protection, breathable materials, adjustable sizing, and travel-friendly construction that makes packing easy without sacrificing style.

From beach vacations and island escapes to European tours and resort retreats, you'll find hats designed to keep you comfortable while complementing your vacation wardrobe.

No matter where your travels take you, enjoy lightweight comfort, reliable UV protection, and timeless style with a vacation hat that's ready for every destination.

Packing Methods for Different Hat Styles

Frequently Asked Questions about Vacation Hats – Stylish Sun Hats for Every Getaway

What is the best hat to wear on vacation?

The best vacation hats are lightweight, packable, and provide excellent sun protection. Wide brim sun hats, bucket hats, straw hats, and travel hats with UPF 50+ are popular choices for beach vacations, cruises, and sightseeing.

Can I pack a vacation hat in my suitcase?

Yes. Many vacation hats are specifically designed for travel and can be packed using methods such as Pack Flat, Stuff the Crown, Soft Taco Fold, or Roll-Up, depending on the hat's construction.

If you are taking a delicate hat for a luxury vacation, you can try our hat carrying tote bag, carry it in a hat box or wear it.

What features should I look for in a vacation hat?

Choose a vacation hat with UPF sun protection, breathable materials, lightweight construction, adjustable sizing, and a recommended packing method that fits your travel style.

Can I wear the same hat for different vacation activities?

Yes. Many vacation hats are versatile enough for sightseeing, beach days, cruises, outdoor dining, hiking, and relaxing by the pool while providing reliable sun protection.

The safest option is to take the hat you feel most comfortable wearing. If you have doubts while you are packing, you likely will not wear it.

Are vacation hats good for year-round travel?

Absolutely. Vacation hats provide sun protection and comfort whether you're traveling in summer or escaping to warm-weather destinations during the cooler months. Quality packable vacation hats are designed to recover their shape after unpacking when packed according to the manufacturer's recommendations.