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Adjustable Size Hats

  • Rip Stop Cotton Boonie with Floatable Brim - DPC Outdoor Hats Bucket Hat Dorfman Hat Co.
    Rip Stop Cotton Boonie with Floatable Brim - DPC Outdoor Hats Bucket Hat Dorfman Hat Co. MC428-PUTTY2 Putty Medium

    Rip Stop Cotton Boonie with Floatable Brim - DPC Outdoor Hats

    $ 39.00

    Pigment dyed rip stop cotton boonie hat. Dimensional bound brim, 3.75" wide front and back, 3" sides. Floatable brim makes this a great fishing, sa...

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    $ 39.00
  • Open Weave Seagrass Straw Fedora - Tidal Tom Hats Fedora Hat Tidal Tom HTT1010B-XL Brown XL (60-61 cm)
    Open Weave Seagrass Straw Fedora - Tidal Tom Hats Fedora Hat Tidal Tom HTT1010A-ML Navy M/L (57-59 cm)

    Open Weave Seagrass Straw Fedora - Tidal Tom Hats

    $ 27.50

    Refine your warm-weather style with this natural seagrass straw fedora hat for men, designed for both comfort and timeless appeal. Featuring a clas...

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    $ 27.50
  • Crocheted Summer Cloche - Callanan Handmade Hats Wide Brim Hat Callanan Hats CR257WH White M/L (58 cm)

    Crocheted Summer Cloche - Callanan Handmade Hats

    $ 79.00

    Crafted by the talented hands of John Callanan, this charming cloche brings vintage flair to your summer wardrobe. Hand-crocheted with shimmering L...

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    $ 79.00
  • 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
  • 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
  • Victoria Cap - Wallaroo Hat Company Facesaver Hat Wallaroo Hats
    Victoria Cap - Wallaroo Hat Company Facesaver Hat Wallaroo Hats

    Victoria Cap - Wallaroo Hat Company

    $ 53.00

    Introducing the Victoria Cap, a brand-new addition to Wallaroo’s iconic Victoria collection. This innovative sun cap blends the comfort of a classi...

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    $ 53.00
  • Cotton Sun Hat with Ponytail Opening - Scala Hats for Women Wide Brim Hat Scala Hats SCA11739-WHBLK White / Black M/L (57 - 58 cm)
    Cotton Sun Hat with Ponytail Opening - Scala Hats for Women Wide Brim Hat Scala Hats

    Cotton Sun Hat with Ponytail Opening - Scala Hats for Women

    $ 37.00

    Designed for active women who refuse to compromise on style or sun protection, this Scala cotton sun hat combines practical functionality with eleg...

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    $ 37.00
  • River Knit Western Hat Tassel Band - Sun 'N' Sand Hats Cowboy Hat Sun N Sand Hats HH3147B Natural OS (58 cm)
    River Knit Western Hat Tassel Band - Sun 'N' Sand Hats Cowboy Hat Sun N Sand Hats

    River Knit Western Hat Tassel Band - Sun 'N' Sand Hats

    $ 42.00

    Embrace your bold style with this versatile knit western hat, designed for the confident woman who refuses to blend in. The classic off-white hue p...

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    $ 42.00
  • Multi Color Shapeable Brim Western Hat - Cappelli Straworld Cowboy Hat Cappelli Straworld
    Multi Color Shapeable Brim Western Hat - Cappelli Straworld Cowboy Hat Cappelli Straworld CSW415-AQU Aqua

    Multi Color Shapeable Brim Western Hat - Cappelli Straworld

    $ 32.00

    Bring some personality to your western wardrobe with this vibrant multi-color braided cowgirl hat. Featuring a distinctive dented crown and front p...

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    $ 32.00
  • Paloma Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Paloma Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Paloma Fedora by Wallaroo Hat Company

    $ 81.00

    The Paloma Fedora combines natural raffia craftsmanship with relaxed luxury, making it an ideal summer hat for beach vacations, poolside lounging, ...

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    $ 81.00
  • Everett Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats EVRT-MC-M Mixed Camel M/L (59 cm)
    Everett Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Everett Fedora by Wallaroo Hat Company

    $ 69.00

    Designed specifically for golfers, the Everett brings together classic fedora style and high-performance bamboo fabric to keep you protected and co...

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

    Montecito by Wallaroo Hat Company

    $ 69.00

    The Montecito Broad-Brimmed Rancher hat offers a coastal-chic look with its soft, woven texture and relaxed brim. This rancher-style wide-brim hat ...

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    $ 69.00
  • Quinn by Wallaroo Hat Company Cowboy Hat Wallaroo Hats
    Quinn by Wallaroo Hat Company Cowboy Hat Wallaroo Hats

    Quinn by Wallaroo Hat Company

    $ 85.00

    The Quinn is a romantic western hat inspired by Jane Seymour's role in Dr. Quinn, Medicine Woman that combines rustic charm with modern sun protect...

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    $ 85.00
  • Nosara by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Nosara by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Nosara by Wallaroo Hat Company

    $ 81.00

    The Nosara Wide Brim Sun Hat is handcrafted from natural raffia straw for a rich, authentic texture that captures the spirit of island living. Its ...

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    $ 81.00
  • Two Tone UV Blocking Safari Hat - Karen Keith Hats Safari Hat Great hats by Karen Keith BT14-F Toast

    Two Tone UV Blocking Safari Hat - Karen Keith Hats

    $ 30.00

    Elevate your outdoor style with this braided toyo safari hat, designed for both elegance and high-performance sun protection. The tweed toast-color...

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    $ 30.00
  • Braided Raffia Up Brim Hat with Chin Cord - Scala Hats Kettle Brim Hat Scala Hats
    Braided Raffia Up Brim Hat with Chin Cord - Scala Hats Kettle Brim Hat Scala Hats LR784 Natural Large (59 cm)

    Braided Raffia Up Brim Hat with Chin Cord - Scala Hats

    $ 51.99

    Discover timeless elegance with this stunning Scala Hats braided raffia creation. Featuring a gracefully rounded crown and distinctive kettle brim ...

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    $ 51.99
  • Carkella Vivian by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Vivian by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Vivian by Wallaroo Hat Company

    $ 71.00

    The Vivian offers a sophisticated silhouette with its gently upturned brim and structured safari crown. Designed with Carkella’s magnetic emblem sy...

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    $ 71.00
  • Rio Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Rio Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Rio Fedora by Wallaroo Hat Company

    $ 61.00

    Introducing the Rio Women’s Fedora, a NEW 2026 Wallaroo style designed for women who want instant, effortless sun protection without sacrificing st...

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    $ 61.00
  • Capybura Toyo Straw Western Hat - Panama Jack Hats Cowboy Hat Panama Jack Hats PJL748-NAT Natural OS (60 cm)
    Capybura Toyo Straw Western Hat - Panama Jack Hats Cowboy Hat Panama Jack Hats PJL748-TAN Tan OS (60 cm)

    Capybura Toyo Straw Western Hat - Panama Jack Hats

    $ 37.00

    Capture the perfect beachy boho vibe with the Capybura Toyo Straw Western Hat by Panama Jack. Crafted from crocheted toyo straw, it offers a lightw...

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    $ 37.00
  • Open Weave Straw Fedora with Turtle Tape Band - Tidal Tom Hats Fedora Hat Tidal Tom HTT1274 ML Natural M/L (59 cm)

    Open Weave Straw Fedora with Turtle Tape Band - Tidal Tom Hats

    $ 37.00

    Stay cool and polished with this woven straw fedora hat for men, designed for breathable comfort and classic style. Featuring a center-dent crown w...

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    $ 37.00
  • Quick Dry Nylon UV Bill Cap with Neck Cape - Sun 'N' Sand Hats Trail Hat Sun N Sand Hats HH3346A White

    Quick Dry Nylon UV Bill Cap with Neck Cape - Sun 'N' Sand Hats

    $ 34.50

    Experience ultimate sun protection with this innovative quick-dry nylon cap designed for active outdoor enthusiasts. The expansive 4-inch brim shie...

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    $ 34.50
  • Microfiber Wide Bill Visor for Men - Juniper UV Wear Visor Cap MegaCI
    Microfiber Wide Bill Visor for Men - Juniper UV Wear Visor Cap MegaCI J7257-GREY Grey

    Microfiber Wide Bill Visor for Men - Juniper UV Wear

    $ 15.00

    Elevate your game with this premium microfiber visor designed for athletes who demand excellence. The expansive bill is 9" wide with 3.25" peak del...

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    $ 15.00
  • Braid Straw Up Turned Brim Safari Hat - Angela & William Hats Safari Hat Epoch Hats
    Braid Straw Up Turned Brim Safari Hat - Angela & William Hats Safari Hat Epoch Hats F6040 Natural Large (58-59 cm)

    Braid Straw Up Turned Brim Safari Hat - Angela & William Hats

    $ 32.00

    Ready to explore in style? This unisex safari hat brings serious fun to sun protection with its signature upturned brim and shapeable design. The 3...

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    $ 32.00
  • Greenwich by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Greenwich by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Greenwich by Wallaroo Hat Company

    $ 73.00

    The Greenwich brings polished sophistication to sun-safe style with its gently upturned brim and beautifully structured safari crown. Designed for ...

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    $ 73.00

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.