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Adjustable Size Hats

  • Lady Brett Cloche by Wallaroo Hat Company Cloche Wallaroo Hats
    Lady Brett Cloche by Wallaroo Hat Company Cloche Wallaroo Hats

    Lady Brett Cloche by Wallaroo Hat Company

    $ 71.00

    This newest addition to Wallaroo’s Jane Seymour Collection captures the actress’s signature elegance with a classic cloche silhouette that never go...

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    $ 71.00
  • Adora® Wool Hat - Up Brim Cloche Hat with Boucle Trim Cloche Adora Hats
    Adora® Wool Hat - Up Brim Cloche Hat with Boucle Trim Cloche Adora Hats AD1270A Black OS
    Sale

    Adora® Wool Hat - Up Brim Cloche Hat with Boucle Trim

    Original Price $ 48.00
    Current Price $ 24.00

    This elegant wool felt cloche features a gracefully turned-up brim approximately 3 inches wide, complemented by a charming bow positioned at the ba...

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    Original Price $ 48.00
    Current Price $ 24.00
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  • Fine Braid Fedora with Macrame Band - Sun 'n' Sand® Hats Fedora Hat Sun N Sand Hats HH3023 Natural OS (57 cm)

    Fine Braid Fedora with Macrame Band - Sun 'n' Sand® Hats

    $ 34.00

    Elevate your sun-ready style with this sophisticated fine braid fedora, designed for the modern woman who refuses to compromise on elegance or prot...

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    $ 34.00
  • Eden Knit Fedora with Belt Band - Sun 'n' Sand® Hats Fedora Hat Sun N Sand Hats HH3051A Natural OS (57 cm)

    Eden Knit Fedora with Belt Band - Sun 'n' Sand® Hats

    $ 31.00

    Own your confidence with the Eden Knit Fedora, the perfect companion for spring to fall seasons. Crafted from breathable lightweight knit, this hat...

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    $ 31.00
  • Brielle Knit Fedora with Colorful Band - Sun 'n' Sand® Hats Fedora Hat Sun N Sand Hats HH3148A Natural M/L (58.5 cm)

    Brielle Knit Fedora with Colorful Band - Sun 'n' Sand® Hats

    $ 34.00

    Step into confidence with the Brielle Knit Fedora, your go-to accessory for spring through early fall adventures. Crafted from breathable knit fabr...

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    $ 34.00
  • Flamingo Bucket Hat - Sun 'N' Sand Hats Bucket Hat Sun N Sand Hats HH3349 Flamingo OS

    Flamingo Bucket Hat - Sun 'N' Sand Hats

    $ 28.50

    Step into summer with confidence wearing this striking Flamingo Bucket Hat, designed for those who refuse to compromise on style or protection. Bui...

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    $ 28.50
  • Straw Cowboy Hat with Rhinestone Gem Band - Boardwalk Hats Cowboy Hat Boardwalk Style Hats DA1343-TAN Tan OS
    Straw Cowboy Hat with Rhinestone Gem Band - Boardwalk Hats Cowboy Hat Boardwalk Style Hats

    Straw Cowboy Hat with Rhinestone Gem Band - Boardwalk Hats

    $ 29.00

    Embrace the perfect blend of style and practicality with this striking straw cowboy hat. Crafted from lightweight straw with a classic dented crown...

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    $ 29.00
  • Carkella Emery Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Carkella Emery Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Carkella Emery Fedora by Wallaroo Hat Company

    $ 69.00

    The Emery blends resort-chic style with clever functionality. Its structured fedora crown pairs beautifully with a frayed, textured brim for a rela...

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

    Aspen by Wallaroo Hat Company

    $ 75.00

    The Aspen Safari Hat brings timeless sophistication to fall and winter adventures. Crafted from high-quality wool felt, it offers a structured shap...

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    $ 75.00
  • Winter Motif Kid's Fleece Snap Brim Fedora Hat - JSA Kids Hats Fedora Hat Jeanne Simmons Accessories JS1148 Black XS (53 cm)
    Sale

    Winter Motif Kid's Fleece Snap Brim Fedora Hat - JSA Kids Hats

    Original Price $ 12.00
    Current Price $ 5.99

    Introduce your child to cozy style with this charming fleece fedora featuring a festive winter motif in burgundy, grey, and ivory tones. The snap b...

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    Original Price $ 12.00
    Current Price $ 5.99
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  • Wool Felt Cloche Hat with Embroidered Sequin Band - Adora® Hats Cloche Adora Hats AD980bn Brown
    Sale

    Wool Felt Cloche Hat with Embroidered Sequin Band - Adora® Hats

    Original Price $ 32.00
    Current Price $ 16.00

    This elegant wool felt cloche features a distinctive bucket silhouette with an asymmetrical brim that tapers from 3 inches at the front to 2 inches...

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    Original Price $ 32.00
    Current Price $ 16.00
    Sale
  • Striped Wide Brim Summer Floppy Hat - Red and Navy Wide Brim Sun Hat Boardwalk Style Hats da1786rd Red/Navy Medium (57 cm)

    Striped Wide Brim Summer Floppy Hat - Red and Navy

    $ 25.00

    Shield yourself from the sun in timeless style with this classic capeline sun hat. Featuring a generous 4-inch floppy brim and UPF 50+ protection, ...

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    $ 25.00
  • Mineral Stone Band Safari Hat by Tommy Bahama Safari Hat Tommy Bahama Hats
    Mineral Stone Band Safari Hat by Tommy Bahama Safari Hat Tommy Bahama Hats tbwl82nt Natural
    Sale

    Mineral Stone Band Safari Hat by Tommy Bahama

    Original Price $ 84.00
    Current Price $ 69.95

    Make every sunny moment unforgettable with this stunning Tommy Bahama women’s raffia safari hat, designed to combine natural texture with eye-catch...

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    Original Price $ 84.00
    Current Price $ 69.95
    Sale
  • Navy Macrame Brim Floppy Hat - Tommy Bahama Floppy Hat Tommy Bahama Hats tbwl91nv Navy

    Navy Macrame Brim Floppy Hat - Tommy Bahama

    $ 36.00

    Make a bold, resort-ready statement with this two-tone floppy brim hat crafted from braided navy straw and macramé raffia sections. Designed for st...

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    $ 36.00
  • Faux Leather Bucket Hat for Women - Adora® Hats Bucket Hat Adora Hats
    Faux Leather Bucket Hat for Women - Adora® Hats Bucket Hat Adora Hats AD1471D Navy OS (57 cm)
    Sale

    Faux Leather Bucket Hat for Women - Adora® Hats

    Original Price $ 24.00
    Current Price $ 12.00

    Give the everyday bucket hat a sophisticated update with this Adora® faux leather bucket hat for women. The smooth faux leather finish creates a cl...

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    Original Price $ 24.00
    Current Price $ 12.00
    Sale
  • Structured Fashion Suede Safari Hat - Adora® Wool Hats Safari Hat Adora Hats AD1606A Charcoal OS (57 cm)
    Structured Fashion Suede Safari Hat - Adora® Wool Hats Safari Hat Adora Hats AD1606B Tan OS (57 cm)
    Sale

    Structured Fashion Suede Safari Hat - Adora® Wool Hats

    Original Price $ 38.00
    Current Price $ 19.00

    Make a sophisticated statement in this Adora® structured faux suede safari hat, designed with clean lines, rich texture, and a tailored silhouette....

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    Original Price $ 38.00
    Current Price $ 19.00
    Sale
  • Small Brim Chenille Knit Boater Hat - Adora Wool Hat® Cloche Adora Hats AD1539A Tan OS
    Small Brim Chenille Knit Boater Hat - Adora Wool Hat® Cloche Adora Hats AD1539C Navy OS
    Sale

    Small Brim Chenille Knit Boater Hat - Adora Wool Hat®

    Original Price $ 32.00
    Current Price $ 16.00

    Enjoy the polished look of a structured hat with the softness and flexibility of knitwear in this Adora® women's chenille boater hat. Its velvety c...

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    Original Price $ 32.00
    Current Price $ 16.00
    Sale
  • Shapeable Brim Grey Knit Wool Hat - Adora Wool Hat® Cloche Adora Hats AD1325A Grey OS
    Sale

    Shapeable Brim Grey Knit Wool Hat - Adora Wool Hat®

    Original Price $ 32.00
    Current Price $ 16.00

    Designed for women who want a packable winter hat without sacrificing style, this Adora® knit wool hat combines soft comfort, a flattering silhouet...

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    Original Price $ 32.00
    Current Price $ 16.00
    Sale
  • Wide Brim Winter Hat with Tribal Pattern Woven Band - Adora® Hats Floppy Hat Adora Hats AD1573B Navy OS
    Sale

    Wide Brim Winter Hat with Tribal Pattern Woven Band - Adora® Hats

    Original Price $ 41.00
    Current Price $ 15.00

    Winter poly-felt wide brim hat. Dome crown. Tribal pattern woven band with braided faux suede tie. Stiff brim bound with matching woven ribbon, 4.2...

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    Original Price $ 41.00
    Current Price $ 15.00
    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.