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Vacation Hats – Stylish Sun Hats for Every Getaway

  • 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
  • Two Tone Up-Brim Sun Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories JS8210 Black / White
    Two Tone Up-Brim Sun Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories JS8212 Black / Tan

    Two Tone Up-Brim Sun Hat - Jeanne Simmons Hats

    $ 34.00

    Refined, packable, and effortlessly chic, this two-tone upturned brim hat is designed for modern travelers who demand both style and performance. T...

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    $ 34.00
  • 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
  • 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
  • Wide Brim Beach Hat with Black Band & Bow - Sun 'N' Sand Hats Wide Brim Sun Hat Sun N Sand Hats HH2039A Ivory OS (57 cm)

    Wide Brim Beach Hat with Black Band & Bow - Sun 'N' Sand Hats

    $ 42.00

    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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    $ 42.00
  • Darby Cloche by Wallaroo Hat Company Cloche Wallaroo Hats DARB- Ivory/Blue OS (58 cm)
    Darby Cloche by Wallaroo Hat Company Cloche Wallaroo Hats

    Darby Cloche by Wallaroo Hat Company

    $ 61.00

    Introducing the Darby Cloche—a timeless two-tone design that celebrates effortless elegance. This ivory beauty features striking contrast stitching...

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    $ 61.00
  • Shapeable Ribbon Brim Sun Hat with Straw Crown - Scala Hats Wide Brim Hat Scala Hats SCA11855-BLK Black
    Shapeable Ribbon Brim Sun Hat with Straw Crown - Scala Hats Wide Brim Hat Scala Hats SCA11855-NAVY Navy

    Shapeable Ribbon Brim Sun Hat with Straw Crown - Scala Hats

    $ 34.00

    Introducing a new Spring 2026 style from Scala Hats: a classic statement sun hat designed to deliver bold coverage and polished elegance in one eas...

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    $ 34.00
  • Petite Darby Cloche by Wallaroo Hat Company Cloche Wallaroo Hats PDARB-IB Ivory/Black S (55 cm)
    Petite Darby Cloche by Wallaroo Hat Company Cloche Wallaroo Hats

    Petite Darby Cloche by Wallaroo Hat Company

    $ 61.00

    The Petite Darby by Wallaroo brings timeless cloche style to smaller head sizes, offering a beautifully scaled vintage silhouette that flatters eff...

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    $ 61.00
  • Lady Brett Cloche by Wallaroo Hat Company Cloche Wallaroo Hats
    Lady Brett Cloche by Wallaroo Hat Company Cloche Wallaroo Hats

    Lady Brett Cloche by Wallaroo Hat Company

    $ 71.00

    This newest addition to Wallaroo’s Jane Seymour Collection captures the actress’s signature elegance with a classic cloche silhouette that never go...

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    $ 71.00
  • Denver Cowboy by Wallaroo Hats Cowboy Hat Wallaroo Hats
    Denver Cowboy by Wallaroo Hats Cowboy Hat Wallaroo Hats

    Denver Cowboy by Wallaroo Hats

    $ 73.00

    This women’s Flexi-Weave Cowboy Hat blends the classic Western silhouette with lightweight, modern comfort. The soft, flexible construction lets yo...

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    $ 73.00
  • Crocheted Toyo Up Brim Summer Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories JS1110-IVO Ivory OS (57 cm)

    Crocheted Toyo Up Brim Summer Hat - Jeanne Simmons Hats

    $ 25.00

    Embrace effortless summer style with this beautifully crafted crocheted toyo hat. Featuring a shapeable 2.5" brim with an elegant 1" upturned edge,...

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    $ 25.00
  • Two Tone Summer Cloche with Contrast Trim - Karen Keith Cloche Great hats by Karen Keith BT15-NTTW Natural Tweed 58 cm
    Two Tone Summer Cloche with Contrast Trim - Karen Keith Cloche Great hats by Karen Keith BT15-BKTW Black Tweed 58 cm

    Two Tone Summer Cloche with Contrast Trim - Karen Keith

    $ 23.00

    Discover the perfect balance of sophistication and practicality with this elegant two-tone cloche. Crafted from a supremely soft paper-poly blend, ...

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    $ 23.00
  • Salt Water Cotton Canvas Beach Hat with Frayed Brim - Makai Hats Floppy Hat Makai Hat
    Salt Water Cotton Canvas Beach Hat with Frayed Brim - Makai Hats Floppy Hat Makai Hat MA159-TAN Tan
    Sale

    Salt Water Cotton Canvas Beach Hat with Frayed Brim - Makai Hats

    Original Price $ 70.00
    Current Price $ 54.99

    Enjoy effortless coastal style with the Salt Water Cotton Canvas Beach Hat by Makai, designed for comfort, coverage, and everyday versatility. Made...

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    Original Price $ 70.00
    Current Price $ 54.99
    Sale
  • Split Brim Sun Hat with Straw Bow - Scala Collection Hats Wide Brim Hat Scala Hats
    Split Brim Sun Hat with Straw Bow - Scala Collection Hats Wide Brim Hat Scala Hats LP170-TT Toast Medium (57 cm)

    Split Brim Sun Hat with Straw Bow - Scala Collection Hats

    $ 39.99

    Embrace effortless elegance with this timeless wide-brim design that commands attention. The innovative butterfly split brim moves with you, offeri...

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    $ 39.99
  • Kids' Scrunchie by Wallaroo Hat Company Wide Brim Sun Hat Wallaroo Hats KSCR-HD Hydrangea / White Extra-Small (52 cm)
    Kids' Scrunchie by Wallaroo Hat Company Wide Brim Sun Hat Wallaroo Hats

    Kids' Scrunchie by Wallaroo Hat Company

    $ 33.00

    The Kids’ Scrunchie is designed with little adventurers in mind. Soft, flexible, and easily packable, it rolls or folds into a tiny space and sprin...

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    $ 33.00
  • Wide Brim Straw Ponytail Facesaver Sun Hat - Boardwalk Hats Wide Brim Hat Boardwalk Style Hats
    Wide Brim Straw Ponytail Facesaver Sun Hat - Boardwalk Hats Wide Brim Hat Boardwalk Style Hats DA1929-IVO Ivory Tweed OS

    Wide Brim Straw Ponytail Facesaver Sun Hat - Boardwalk Hats

    $ 27.00

    Stay protected and stylish with this Wide Brim Straw Ponytail Facesaver Sun Hat from Boardwalk Hats. Featuring a robust UPF 50+ rating that blocks ...

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    $ 27.00
  • Ribbon and Straw Wide Brim Ponytail Sun Hat - Boardwalk Hats Visor Cap Boardwalk Style Hats
    Ribbon and Straw Wide Brim Ponytail Sun Hat - Boardwalk Hats Visor Cap Boardwalk Style Hats DA1930-IVBK Ivory / Black OS

    Ribbon and Straw Wide Brim Ponytail Sun Hat - Boardwalk Hats

    $ 25.00

    Keep the sun at bay with this versatile Ribbon and Straw Wide Brim Ponytail Sun Hat from Boardwalk Hats. Engineered with UPF 50+ protection, the ge...

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    $ 25.00

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.