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Adjustable Size Hats

  • Large Bill Flap Cap - Milani Hats Cap Milani Hats
    Large Bill Flap Cap - Milani Hats Cap Milani Hats F006-NG Neon Green OS (56-60 cm)
    Sale
    Original Price $ 18.00
    Current Price $ 12.99
    Milani Hats

    Large Bill Flap Cap - Milani Hats

    This bold four-panel cap commands attention with its oversized 2.75" bill and protective neck flap that shields you from sun exposure. Engineered f...

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    Original Price $ 18.00
    Current Price $ 12.99
    Sale
  • No Fly Zone Fishing Hat - Stetson® and Scala Hats Bucket Hat Stetson Hats
    No Fly Zone Fishing Hat - Stetson® and Scala Hats Bucket Hat Stetson Hats stc199NTM Khaki Stetson Hats Medium (22.5")
    from $ 35.00
    Stetson Hats

    No Fly Zone Fishing Hat - Stetson® and Scala Hats

    Meet the ultimate “all-the-gadgets” bucket hat—built for anyone who wants comfort, coverage, and clever outdoor performance in one easy, everyday s...

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    from $ 35.00
  • Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Petite Sedona by Wallaroo Hat Company

    The Petite Sedona brings rustic charm and sun-smart performance to smaller head sizes. Its woven paper-braid texture offers breathable comfort, whi...

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    $ 61.00
  • Palm Beach Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Palm Beach Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 65.00
    Wallaroo Hats

    Palm Beach Safari by Wallaroo Hat Company

    The Palm Beach Safari Hat combines modern structure with lightweight comfort, making it a top choice for men and women who want dependable sun prot...

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    $ 65.00
  • Sedona Fedora, M & XL - Wallaroo Hat Company Safari Hat Wallaroo Hats
    Sedona Fedora, M & XL - Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Sedona Fedora, M & XL - Wallaroo Hat Company

    The full-size Sedona Safari Hat blends a relaxed woven texture with excellent sun protection for warm-weather outings. Its wide downturned brim pro...

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    $ 61.00
  • Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons
    Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons js1239-TAN Tan XS (55 cm)
    $ 24.00
    Jeanne Simmons

    Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats

    Meet your new favorite travel companion! This charming paper braid fedora is designed specifically for smaller heads and brings instant personality...

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    $ 24.00
  • Charlie Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Charlie Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Charlie Fedora by Wallaroo Hat Company

    Designed with a contemporary silhouette, the Charlie Fedora pairs clean lines with effortless comfort. The structured crown and medium brim create ...

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    $ 61.00
  • Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 65.00
    Wallaroo Hats

    Petite Palm Beach by Wallaroo Hat Company

    The Petite Palm Beach Safari Hat delivers packable convenience and classic outdoor style for smaller head sizes. Its crushable construction allows ...

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    $ 65.00
  • Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats Bucket Hat Dorfman Hat Co.
    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats Bucket Hat Dorfman Hat Co. MC2-KAKI1 Khaki Small (55 cm)
    $ 26.99
    Dorfman Hat Co.

    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats

    Trailer DPC Outdoor hats for hiking. Supplex® nylon boonie with vented mesh crown. Covered underbrim, 3" wide stitched brim. Wide elastic CoolMax® ...

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    $ 26.99
  • Carter Fedora by Wallaroo Hats Safari Hat Wallaroo Hats CART-IV-M Ivory/Stone M/L (59 cm)
    Carter Fedora by Wallaroo Hats Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Carter Fedora by Wallaroo Hats

    The Carter is a sophisticated fedora hat with clean lines. Crafted from lightweight, breathable materials, it ensures comfort even on extremely hot...

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    $ 61.00
  • Wide Brim Unisex Gardening Hat by JSA - Large and XL Sizes Safari Hat Jeanne Simmons
    Wide Brim Unisex Gardening Hat by JSA - Large and XL Sizes Safari Hat Jeanne Simmons js6989wt-M Wheat Tweed Medium (57 cm)
    $ 34.00
    Jeanne Simmons

    Wide Brim Unisex Gardening Hat by JSA - Large and XL Sizes

    Protect yourself while tending your garden with this versatile unisex hat designed for serious sun exposure. The generous 5-inch brim shields your ...

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    $ 34.00
  • Supplex® Nylon Boonie with Covered Underbrim - DPC Global Hats Bucket Hat Dorfman Hat Co.
    Supplex® Nylon Boonie with Covered Underbrim - DPC Global Hats Bucket Hat Dorfman Hat Co. MC1-KAKI1 Khaki Small (55 cm)
    $ 24.00
    Dorfman Hat Co.

    Supplex® Nylon Boonie with Covered Underbrim - DPC Global Hats

    Evergreen DPC Outdoor hats for fishing. Supplex® nylon boonie hat. Covered underbrim reduces glare. Stitched brim, 3.25" wide. Wide elastic CoolMax...

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    $ 24.00
  • Outback Hat by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Outback Hat by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Outback Hat by Wallaroo Hat Company

    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
  • Avery Wide Brim Golf Hat - Wallaroo Hats Fedora Hat Wallaroo Hats
    Avery Wide Brim Golf Hat - Wallaroo Hats Fedora Hat Wallaroo Hats
    $ 69.00
    Wallaroo Hats

    Avery Wide Brim Golf Hat - Wallaroo Hats

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

    Carkella Del Mar Fedora by Wallaroo Hat Company

    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
  • 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)
    $ 33.00
    Dorfman Hat Co.

    Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear

    DPC Outdoor Hats for men and women. Supplex® materials provide cottony soft comfort, while shrink and fade resistant, and faster drying. This booni...

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    $ 33.00
  • Carkella Fairway Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Fairway Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 67.00
    Wallaroo Hats

    Carkella Fairway Fedora by Wallaroo Hat Company

    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
  • Palm Beach Carkella by Wallaroo Hats Safari Hat Wallaroo Hats PLMBCHMBKM Black M/L (59 cm)
    Palm Beach Carkella by Wallaroo Hats Safari Hat Wallaroo Hats
    $ 65.00
    Wallaroo Hats

    Palm Beach Carkella by Wallaroo Hats

    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
  • Palmer Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Palmer Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Palmer Safari by Wallaroo Hat Company

    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
  • 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)
    $ 28.75
    Sun N Sand Hats

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

    Tribal band fedora hat for small heads. Braid dented crown with pinched front. Tribal pattern woven band with raffia loop. Milan braid brim, 2" wid...

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    $ 28.75
  • 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)
    $ 16.50
    Great hats by Karen Keith

    Cotton Bucket Hat with Drawstring - Karen Keith Hats

    Traditional cotton bucket hat for men and women. Narrow brim, 2.5" wide with stitching detail. Square crown, 4" deep. Inner drawstring to reduce si...

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    $ 16.50
  • Logan Unisex Safari Hat - Wallaroo Hats Safari Hat Wallaroo Hats
    Logan Unisex Safari Hat - Wallaroo Hats Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Logan Unisex Safari Hat - Wallaroo Hats

    The Logan Safari Hat delivers durable performance with a relaxed, masculine profile. Its wide brim provides comfortable shade, while breathable fab...

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    $ 61.00
  • 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
    $ 32.00
    Dorfman Hat Co.

    Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear

    Supplex® materials provide cottony soft comfort, while shrink and fade resistant, and faster drying. This boonie style men's hat will be a great co...

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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
    Original Price $ 49.00
    Current Price $ 26.00
    Wallaroo Hats

    St. Tropez Trilby by Wallaroo Hat Company

    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

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.