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Adjustable Size Hats

  • 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
  • Adora® Wool Hat - Wool Felt Fedora Grosgrain Ribbon Trim Fedora Hat Adora Hats AD1604B Tan OS
    Adora® Wool Hat - Wool Felt Fedora Grosgrain Ribbon Trim Fedora Hat Adora Hats

    Adora® Wool Hat - Wool Felt Fedora Grosgrain Ribbon Trim

    $ 58.00

    This classic wool felt fedora delivers understated sophistication with versatile styling options. The structured teardrop crown features a front pi...

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    $ 58.00
  • Crushable Wool Felt Western Hat with Aztec Band - Scala Hats Cowboy Hat Scala Hats
    Crushable Wool Felt Western Hat with Aztec Band - Scala Hats Cowboy Hat Scala Hats LF258-CHOC Chocolate Medium (57 cm)

    Crushable Wool Felt Western Hat with Aztec Band - Scala Hats

    $ 79.99

    Embrace your bold spirit with this stunning crushable wool felt western hat from Scala Hats. Featuring a distinctive C-crown with front pinch and a...

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    $ 79.99
  • Wool Felt Cloche with Beaded Band - Scala Hat Cloche Scala Hats
    Wool Felt Cloche with Beaded Band - Scala Hat Cloche Scala Hats LF275-TP Taupe Medium (57 cm)
    Sale

    Wool Felt Cloche with Beaded Band - Scala Hat

    Original Price $ 68.00
    Current Price $ 24.99

    Embrace timeless elegance with this stunning wool felt cloche, where vintage charm meets modern sophistication. The gracefully sloped brim—3" at th...

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    Original Price $ 68.00
    Current Price $ 24.99
    Sale
  • Two Tone Raffia Cloche Hat - Sophia Collection Cloche Something Special LA
    Two Tone Raffia Cloche Hat - Sophia Collection Cloche Something Special LA WSRA479BN Brown Medium (57 cm)

    Two Tone Raffia Cloche Hat - Sophia Collection

    $ 45.00

    Elevate your warm-weather wardrobe with this hand-crocheted two-tone raffia cloche hat, designed for relaxed elegance and everyday versatility. Cra...

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    $ 45.00
  • Women's Cowboy Hat with Turquoise Concho - Jeanne Simmons Hats Cowboy Hat Jeanne Simmons Accessories JS1355-GY Grey
    Women's Cowboy Hat with Turquoise Concho - Jeanne Simmons Hats Cowboy Hat Jeanne Simmons Accessories JS1355-BE Beige

    Women's Cowboy Hat with Turquoise Concho - Jeanne Simmons Hats

    $ 38.00

    Saddle up in effortless style with this beautifully crafted straw cowboy hat designed for the modern cowgirl. Made from soft multitone paper braid,...

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    $ 38.00
  • Large Down-Turned Brim Sun Hat - Boardwalk Styles Wide Brim Hat Boardwalk Style Hats DA1774-BNH Brown Heather Medium (57 cm)
    Large Down-Turned Brim Sun Hat - Boardwalk Styles Wide Brim Hat Boardwalk Style Hats

    Large Down-Turned Brim Sun Hat - Boardwalk Styles

    $ 45.00

    Make a striking impression with this elegant Breakfast at Tiffany’s-inspired sun hat, designed to blend classic sophistication with modern versatil...

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    $ 45.00
  • 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
  • Vegan Leather Rancher Hat with Studs and Rings - Scala Hats Safari Hat Scala Hats LW753 Brown Medium (57 cm)
    Vegan Leather Rancher Hat with Studs and Rings - Scala Hats Safari Hat Scala Hats

    Vegan Leather Rancher Hat with Studs and Rings - Scala Hats

    $ 39.99

    This vegan leather rancher delivers Western style with contemporary edge. The structured crown features a subtle front pinch and dented silhouette,...

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    $ 39.99
  • Wool Felt Safari Hat with Braided Suede Band - Scala Hats Safari Hat Scala Hats LF209 Brown Medium (57 cm)

    Wool Felt Safari Hat with Braided Suede Band - Scala Hats

    $ 49.00

    This classic safari hat showcases premium wool felt craftsmanship with a distinctive pinched crown and generously proportioned floppy brim measurin...

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    $ 49.00
  • Calabria Braided Viscose Fedora Hat with Raffia Brim - Brooklyn Hat Co Fedora Hat Brooklyn Hat BKN1577 Brown Medium (22 3/8")
    Sale

    Calabria Braided Viscose Fedora Hat with Raffia Brim - Brooklyn Hat Co

    Original Price $ 62.00
    Current Price $ 30.98

    Weave some style into your wardrobe with this charming Calabria fedora. The crown features rich, multi-toned brown braided viscose that catches the...

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    Original Price $ 62.00
    Current Price $ 30.98
    Sale
  • Two Tone Natural Raffia Beach Hat - Sophia Hat Collection Floppy Hat Something Special LA
    Two Tone Natural Raffia Beach Hat - Sophia Hat Collection Floppy Hat Something Special LA WSRA483BL Blue Medium (57 cm)

    Two Tone Natural Raffia Beach Hat - Sophia Hat Collection

    $ 49.00

    Crocheted natural raffia hat. Wide brim, 5" with contrast color edge.  Twisted raffia tie. Dome crown. Drawstring inside crown to adjust size. Medi...

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    $ 49.00
  • Clear UV Bill Sun Visor with Cushioned Elastic Strap Closure - Sun 'N' Sand Hats Visor Cap Sun N Sand Hats HH3551A Tan OS (49-59 cm)
    Sale

    Clear UV Bill Sun Visor with Cushioned Elastic Strap Closure - Sun 'N' Sand Hats

    Original Price $ 28.50
    Current Price $ 19.99

    Enhance your performance and visibility with this high-function sport visor featuring a unique clear plastic bill for unobstructed surround vision....

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    Original Price $ 28.50
    Current Price $ 19.99
    Sale
  • Laundy Straw Pecos with Pencil Curl - Justin Hats Cowboy Hat Justin Hats JUS11008-SM Brown S/M (57 cm)

    Laundy Straw Pecos with Pencil Curl - Justin Hats

    $ 99.00

    Meet your new favorite sun-blocking companion! This Justin Hats Pecos is built tough with 100% buri braid straw in a sleek dark brown glaze and stu...

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    $ 99.00
  • Linen Sun Hat with Animal Print Scarf - Jeanne Simmons Hats Wide Brim Hat Jeanne Simmons Accessories
    Linen Sun Hat with Animal Print Scarf - Jeanne Simmons Hats Wide Brim Hat Jeanne Simmons Accessories js4020bg Beige

    Linen Sun Hat with Animal Print Scarf - Jeanne Simmons Hats

    $ 23.00

    Elevate your summer wardrobe with this charming linen sun hat from Jeanne Simmons. Crafted from a breathable cotton-linen blend, this sophisticated...

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    $ 23.00

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.