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Adjustable Size Hats

  • Avery Wide Brim Golf Hat - Wallaroo Hats Fedora Hat Wallaroo Hats
    Avery Wide Brim Golf Hat - Wallaroo Hats Fedora Hat Wallaroo Hats

    Avery Wide Brim Golf Hat - Wallaroo Hats

    $ 69.00

    The Avery brings a contemporary twist to the classic fedora silhouette. Made with lightweight, breathable materials, it’s an easy choice for warm-w...

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    $ 69.00
  • Amelia by Wallaroo Hats Kettle Brim Hat Wallaroo Hats AMENT Natural M/L (58 cm)
    Amelia by Wallaroo Hats Kettle Brim Hat Wallaroo Hats

    Amelia by Wallaroo Hats

    $ 59.00

    The Amelia is a charming everyday sun hat designed for easy wear from the beach to the garden. Its soft, flexible weave creates a relaxed look, whi...

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    $ 59.00
  • Outback Hat by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Outback Hat by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Outback Hat by Wallaroo Hat Company

    $ 61.00

    The Outback Safari Hat is designed for active outdoor lifestyles, featuring a durable, breathable construction that stands up to everyday adventure...

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    $ 61.00
  • Carkella Del Mar Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Carkella Del Mar Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Carkella Del Mar Fedora by Wallaroo Hat Company

    $ 61.00

    The Del Mar Fedora combines sleek styling with practical sun protection, making it a favorite on and off the golf course. Its structured crown and ...

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    $ 61.00
  • Petite Straw Safari Hat with Cotton Band - Sunny Dayz™ Safari Hat Sun N Sand Hats HK293C Hibiscus Small (54 cm)
    Petite Straw Safari Hat with Cotton Band - Sunny Dayz™ Safari Hat Sun N Sand Hats HK293B Pineapple Small (54 cm)

    Petite Straw Safari Hat with Cotton Band - Sunny Dayz™

    $ 28.00

    Embrace adventure in every destination with this petite safari hat, designed for the modern traveler who refuses to compromise on style or protecti...

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    $ 28.00
  • Wide Brim Gaucho Hat with Chin Cord - Scala Hats Bolero Hat Scala Hats
    Wide Brim Gaucho Hat with Chin Cord - Scala Hats Bolero Hat Scala Hats LP280-NAT Natural

    Wide Brim Gaucho Hat with Chin Cord - Scala Hats

    $ 42.99

    Embrace timeless elegance with this sophisticated gaucho hat, designed for the woman who commands attention. Featuring a generous 4-inch flat brim ...

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    $ 42.99
  • Tweed Straw Safari Hat - Jeanne Simmons Hats Safari Hat Jeanne Simmons Accessories
    Tweed Straw Safari Hat - Jeanne Simmons Hats Safari Hat Jeanne Simmons Accessories js8250wh White tweed

    Tweed Straw Safari Hat - Jeanne Simmons Hats

    $ 31.00

    Step out in style with this charming tweed straw safari hat from Jeanne Simmons. Crafted from a soft straw and poly blend, it features a classic fe...

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    $ 31.00
  • Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK455 Natural / Pink Small (54 cm)
    Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK454 Tan / Blue Small (54 cm)

    Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats

    $ 28.75

    Embrace your unique style with this petite fedora, expertly crafted for smaller head sizes. Featuring a distinctive tribal-patterned woven band and...

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    $ 28.75
  • Sanibel by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Sanibel by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Sanibel by Wallaroo Hat Company

    $ 61.00

    The Sanibel offers dependable outdoor performance with its wide brim, structured safari crown, and secure chin cord—ideal for windy conditions and ...

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    $ 61.00
  • Tweed Braid Kettle Brim Sun Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories
    Tweed Braid Kettle Brim Sun Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories js8342bkt Black tweed

    Tweed Braid Kettle Brim Sun Hat - Jeanne Simmons Hats

    $ 34.00

    Protect yourself in style with this packable tweed braid kettle brim sun hat, featuring exceptional UPF 50+ sun protection that keeps harmful rays ...

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    $ 34.00
  • Petite Size Straw Cowboy Hat with Chin Cord - Boardwalk Style Cowboy Hat Boardwalk Style Hats
    Petite Size Straw Cowboy Hat with Chin Cord - Boardwalk Style Cowboy Hat Boardwalk Style Hats DA2958-NAT Natural Small (55 cm)

    Petite Size Straw Cowboy Hat with Chin Cord - Boardwalk Style

    $ 25.00

    Step into your power with this petite-sized western straw hat, purposefully crafted for smaller head dimensions. The distinctive pinched crown and ...

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    $ 25.00
  • Tahiti Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats
    Tahiti Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats

    Tahiti Cowboy by Wallaroo Hat Company

    $ 71.00

    The Tahiti Cowboy Hat brings tropical Western style to summer outfits with its hand-crocheted raffia construction and sculpted cowboy crown accente...

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    $ 71.00
  • Petite Catalina Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats
    Petite Catalina Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats

    Petite Catalina Cowboy by Wallaroo Hat Company

    $ 69.00

    The Petite Catalina Cowboy Hat brings classic Western styling to smaller head sizes, offering a flattering silhouette with breezy warm-weather comf...

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    $ 69.00
  • Palmer Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Palmer Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Palmer Safari by Wallaroo Hat Company

    $ 61.00

    The Palmer Fedora features clean lines and a breathable woven texture that makes it a stylish and practical warm-weather hat. The structured crown ...

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    $ 61.00
  • Downturned Big Brim Asymmetrical Summer Hat Wide Brim Hat JEL WSPS608BG Natural tweed
    Downturned Big Brim Asymmetrical Summer Hat Wide Brim Hat JEL WSPS608BN Brown tweed

    Downturned Big Brim Asymmetrical Summer Hat

    $ 25.00

    Packable straw hat with grosgrain ribbon bow. Asymmetrical brim, 4" wide on front and narrows to 2" towards back. Adjustable drawstring inside. Gre...

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    $ 25.00
  • Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats LT209-TOA Toast
    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats

    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats

    $ 36.99

    Escape the sun in style with this stunning Bangkok toyo straw floppy hat from Scala Hats. The distinctive split-back design accommodates low ponyta...

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    $ 36.99
  • Tahiti Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Tahiti Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Tahiti Fedora by Wallaroo Hat Company

    $ 67.00

    The Tahiti Fedora offers natural island-inspired beauty with its hand-crocheted raffia construction and lightweight, breathable feel. The narrow br...

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    $ 67.00
  • Small Kettle Brim Summer Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories
    Small Kettle Brim Summer Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories js8329bk Black OS (57 cm)

    Small Kettle Brim Summer Hat - Jeanne Simmons Hats

    $ 29.00

    Discover effortless sun protection with this charming kettle brim summer hat from Jeanne Simmons. The distinctive upturned brim and dome crown crea...

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    $ 29.00
  • Asymmetrical Big Brim Summer Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Asymmetrical Big Brim Summer Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA221-1 TT Toast tweed Medium (57 cm)

    Asymmetrical Big Brim Summer Hat - Boardwalk Style

    $ 31.00

    Discover effortless sun protection with this sophisticated asymmetrical design. The generous 4-inch front brim tapers gracefully to 3 inches at the...

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    $ 31.00
  • Bangkok Toyo Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats
    Bangkok Toyo Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats LT171BL Black

    Bangkok Toyo Summer Floppy Hat - Scala Hats

    $ 36.99

    Escape to tropical elegance with this stunning Bangkok toyo straw floppy hat from Scala Hats. Featuring a graceful dome crown and an expansive 5-in...

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    $ 36.99

Adjustable hats make it easy to perfect your fit—whether you’re between sizes, sharing a hat, traveling, or simply want a more secure feel on windy days. A better fit doesn’t just feel more comfortable; it also helps your hat stay in place and sit correctly for the coverage you’re counting on.

There are several smart ways hats are made adjustable, including: an interior drawstring inside the sweatband, an elasticized strap with a buckle hidden inside the inner band, an elastic back band with a toggle lock, a classic Velcro® closure, a strap closure with a T-slide, or a small hook-and-loop closure tucked under the sweatband. These built-in systems let you fine-tune the circumference without sacrificing style—so your hat feels snug, secure, and made for you.