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Adjustable Size Hats

  • Cotton Breton Hat with Shapeable Brim - Milani Hat Kettle Brim Hat Milani Hats bh010PK Pink M/L (57 - 58 cm)
    Cotton Breton Hat with Shapeable Brim - Milani Hat Kettle Brim Hat Milani Hats bh010DN Denim M/L (57 - 58 cm) Sale

    Cotton Breton Hat with Shapeable Brim - Milani Hat

    Original Price $ 20.00
    Current Price $ 15.00

    Meet your new go-to summer companion! This charming breton hat features a soft, shapeable cotton construction that bends to your style—literally. T...

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    Original Price $ 20.00
    Current Price $ 15.00
    Sale
  • 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
  • Carkella Fairway Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Fairway Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Fairway Fedora by Wallaroo Hat Company

    $ 67.00

    Designed with golfers in mind, the Fairway blends a stylish fedora shape with a wide protective brim for all-around sun safety. Lightweight and bre...

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    $ 67.00
  • Karen Keith Straw No Back Hat with Ponytail Hole Facesaver Hat Great hats by Karen Keith
    Karen Keith Straw No Back Hat with Ponytail Hole Facesaver Hat Great hats by Karen Keith BT9-CB-I White One Size

    Karen Keith Straw No Back Hat with Ponytail Hole

    $ 29.99

    Embrace sun-smart style with this ingenious straw facesaver hat, designed for active women who refuse to compromise. The open back design celebrate...

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    $ 29.99
  • 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
  • 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
  • Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. mc288whs White S/M (57 cm)

    Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear

    $ 33.00

    Experience the perfect blend of performance and comfort with this Supplex Dimensional Brim Hat. Crafted from innovative Supplex® fabric, it deliver...

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    $ 33.00
  • Palm Beach Carkella by Wallaroo Hats Safari Hat Wallaroo Hats
    Palm Beach Carkella by Wallaroo Hats Safari Hat Wallaroo Hats PLMBCHMBKM Black M/L (59 cm)

    Palm Beach Carkella by Wallaroo Hats

    $ 65.00

    The Palm Beach Safari Hat offers lightweight performance with classic styling, perfect for golf, travel, outdoor adventures, and daily sun protecti...

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    $ 65.00
  • 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
  • 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
  • Cotton Bucket Hat with Drawstring - Karen Keith Hats Bucket Hat Great hats by Karen Keith
    Cotton Bucket Hat with Drawstring - Karen Keith Hats Bucket Hat Great hats by Karen Keith ch50OLM Olive S/M (54-56 cm)

    Cotton Bucket Hat with Drawstring - Karen Keith Hats

    $ 16.50

    Elevate your everyday with this iconic cotton bucket hat, crafted for those who refuse to compromise on style or substance. Featuring a refined 2.5...

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    $ 16.50
  • Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. mc288khs Khaki S/M

    Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear

    $ 32.00

    Conquer every outdoor challenge with a hat designed for those who refuse to compromise. Built from premium Supplex® fabric, this boonie-style hat d...

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    $ 32.00
  • St. Tropez Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats STTR-24-NA Natural / Navy M/L (58 cm)
    St. Tropez Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Sale

    St. Tropez Trilby by Wallaroo Hat Company

    Original Price $ 49.00
    Current Price $ 26.00

    The St. Tropez Trilby features a shorter brim and structured fedora crown, making it a chic option for women and men seeking a compact summer hat. ...

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    Original Price $ 49.00
    Current Price $ 26.00
    Sale
  • Criss Cross Woven Straw Brim Cap - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH3179C Natural M/L (57-59 cm) Hook and Loop Closure
    Criss Cross Woven Straw Brim Cap - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH3179F Navy M/L (57-59 cm) Hook and Loop Closure

    Criss Cross Woven Straw Brim Cap - Sun 'N' Sand Hats

    $ 27.50

    Shield yourself from the sun in style with this versatile straw brim cap featuring an eye-catching crisscross woven band. The generous 3.75" peak d...

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    $ 27.50
  • Supplex Dimensional Brim Hat, White 2XL - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, White 2XL - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC288-WHT5 White XL/2X (61 cm)

    Supplex Dimensional Brim Hat, White 2XL - DPC Outdoor Headwear

    $ 32.00

    Experience the perfect blend of performance and comfort with this DPC Outdoor boonie hat, engineered for adventurers who demand more. Crafted from ...

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    $ 32.00
  • Unisex Gardening Hat with Chin Cord - Large and XL Sizes Safari Hat Jeanne Simmons Accessories js6962l Brown Large (59 cm)
    Unisex Gardening Hat with Chin Cord - Large and XL Sizes Safari Hat Jeanne Simmons Accessories

    Unisex Gardening Hat with Chin Cord - Large and XL Sizes

    $ 27.00

    Shield yourself from the sun with this versatile gardening hat, designed for both men and women who demand protection without compromise. The gener...

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    $ 27.00
  • Supplex Dimensional Brim Hat, Grey - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, Grey - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC288-GREY1 Grey S/M

    Supplex Dimensional Brim Hat, Grey - DPC Outdoor Headwear

    $ 32.00

    Embrace adventure with confidence in this DPC Outdoor boonie-style hat, engineered for serious explorers. The dimensional brim spans 4" front and b...

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    $ 32.00
  • Carkella Sydney Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats SYDFM-DM Denim M/L (58 cm)
    Carkella Sydney Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Sydney Fedora by Wallaroo Hat Company

    $ 51.00

    The Sydney Fedora blends contemporary styling with Carkella’s signature magnetic emblem feature—allowing you to customize your hat with interchange...

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    $ 51.00
  • Elise by Wallaroo Hat Company Safari Hat Wallaroo Hats ELIS-WHBG Natural M/L (58 cm)
    Elise by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Elise by Wallaroo Hat Company

    $ 77.00

    The full-size Elise offers dramatic, full-coverage sun protection with its sweeping extra-wide brim—perfect for tropical vacations, cruises, poolsi...

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    $ 77.00
  • Elegant Wide Brim Straw Hat - Large and Extra-Large Size Safari Hat Jeanne Simmons Accessories
    Elegant Wide Brim Straw Hat - Large and Extra-Large Size Safari Hat Jeanne Simmons Accessories js8001whL White Large (59 cm)

    Elegant Wide Brim Straw Hat - Large and Extra-Large Size

    $ 29.00

    Step into sophistication with this charming wide-brim straw hat, designed for those who love timeless style with a modern twist. Featuring a classi...

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    $ 29.00
  • Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    Explorer by Wallaroo Hat Company Bucket Hat Wallaroo Hats

    Explorer by Wallaroo Hat Company

    $ 57.00

    The Explorer is a performance-driven boonie hat crafted for long days outdoors. Lightweight microfiber keeps it breathable and quick-drying, while ...

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    $ 57.00

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.