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Adjustable Size Hats

  • Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242B Tan Medium (57 cm)
    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242S Natural Medium (57 cm)

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    $ 38.00

    Elevate your sun style with this charming gaucho hat from Caribbean Joe™. Crafted from soft, breathable bangkok toyo, it features a distinctive sun...

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    $ 38.00
  • Butterfly Split Brim Sun Hat with Straw Bow - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Butterfly Split Brim Sun Hat with Straw Bow - Boardwalk Style Wide Brim Hat Boardwalk Style Hats

    Butterfly Split Brim Sun Hat with Straw Bow - Boardwalk Style

    $ 27.00

    Turn heads while staying protected in the Butterfly Split Brim Sun Hat, designed by Boardwalk Style Hat Company with feminine detail. Featuring a u...

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    $ 27.00
  • Shapeable Brim Straw Cowboy Hat - Boardwalk Style Cowboy Hat Boardwalk Style Hats
    Shapeable Brim Straw Cowboy Hat - Boardwalk Style Cowboy Hat Boardwalk Style Hats

    Shapeable Brim Straw Cowboy Hat - Boardwalk Style

    $ 29.00

    Discover versatile sun protection with this shapeable straw cowboy hat designed for the modern woman. The wire-edge brim gives you complete styling...

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    $ 29.00
  • Multitone Polybraid Sun Hat - Milani Hats Wide Brim Sun Hat Milani Hats BB0065bn Brown Medium (57 cm)

    Multitone Polybraid Sun Hat - Milani Hats

    $ 20.00

    Stay cool and protected with this vibrant multitone polybraid sun hat—your poolside and beach essential. The lightweight polybraid weave keeps thin...

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    $ 20.00
  • Sedona Sun Visor by Wallaroo Hat Company Visor Cap Wallaroo Hats
    Sedona Sun Visor by Wallaroo Hat Company Visor Cap Wallaroo Hats

    Sedona Sun Visor by Wallaroo Hat Company

    $ 49.00

    The Sedona Sun Visor blends rustic, woven charm with lightweight performance for warm-weather activities. Its wide brim provides excellent shade fo...

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    $ 49.00
  • Mixed Tone Braid Unisex Safari Hat, Large and XL Sizes - JSA Safari Hat Jeanne Simmons Accessories
    Mixed Tone Braid Unisex Safari Hat, Large and XL Sizes - JSA Safari Hat Jeanne Simmons Accessories js6979bnL Brown Large (59 cm)

    Mixed Tone Braid Unisex Safari Hat, Large and XL Sizes - JSA

    $ 25.00

    Discover versatile sun protection with this unisex safari hat, crafted from mixed-tone braid for effortless style. The structured crown features a ...

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    $ 25.00
  • Crocheted Raffia Up Turned Kettle Brim Hat Kettle Brim Hat Something Special LA
    Crocheted Raffia Up Turned Kettle Brim Hat Kettle Brim Hat Something Special LA WSRA480RT Rust

    Crocheted Raffia Up Turned Kettle Brim Hat

    $ 48.00

    Embrace relaxed coastal style with this beautifully crafted crochet raffia sun hat made from 100% natural raffia. Lightweight and breathable, it of...

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    $ 48.00
  • Multitone Tweed Straw Safari Hat - Jeanne Simmons Hats Safari Hat Jeanne Simmons Accessories
    Multitone Tweed Straw Safari Hat - Jeanne Simmons Hats Safari Hat Jeanne Simmons Accessories

    Multitone Tweed Straw Safari Hat - Jeanne Simmons Hats

    $ 24.00

    This refined multitone tweed straw safari hat from Jeanne Simmons merges classic style with practical functionality. The distinctive fedora-inspire...

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    $ 24.00
  • Packable Straw Souwestern Summer Hat - Sun 'N' Sand Hats Wide Brim Hat Sun N Sand Hats
    Packable Straw Souwestern Summer Hat - Sun 'N' Sand Hats Wide Brim Hat Sun N Sand Hats HH1461B Brown Medium (57 cm)

    Packable Straw Souwestern Summer Hat - Sun 'N' Sand Hats

    $ 29.00

    Embrace timeless style with this vintage-inspired southwestern prairie hat, perfect for your next journey. Featuring a distinctive dome crown with ...

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    $ 29.00
  • Cash Palm Printed Toyo Fedora for Small Heads - Sunny Dayz™ Safari Hat Sun N Sand Hats HK457 Brown Small (53.5 cm)

    Cash Palm Printed Toyo Fedora for Small Heads - Sunny Dayz™

    $ 24.00

    Escape to paradise with this striking palm-printed toyo fedora, designed for those who crave effortless tropical style. Featuring a sophisticated t...

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    $ 24.00
  • 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
  • Polka Dot Band Pinned Up Brim Sun Hat  - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2497B Black / White M (57 cm)
    Polka Dot Band Pinned Up Brim Sun Hat  - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2497A Ivory / Navy M (57 cm)

    Polka Dot Band Pinned Up Brim Sun Hat - Sun 'N' Sand Hats

    $ 24.00

    Make a statement this season with this refined sun hat, showcasing an eye-catching polka dot bow band and an artfully asymmetrical brim pinned grac...

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    $ 24.00
  • Two Tone Raffia Beach Hat with Bow Wide Brim Hat Something Special LA
    Two Tone Raffia Beach Hat with Bow Wide Brim Hat Something Special LA WSraf1353AQ Aqua

    Two Tone Raffia Beach Hat with Bow

    $ 52.00

    Crochet raffia crown. Sewn braid raffia brim. Bound, 5" wide brim with V-cut. Large bow in back. Drawstring inside crown to adjust size. One size. ...

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    $ 52.00
  • 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
  • Victoria Fedora Diva by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Victoria Fedora Diva by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Victoria Fedora Diva by Wallaroo Hat Company

    $ 57.00

    The Victoria Fedora Diva is a stunning new addition to Wallaroo’s iconic Victoria collection, blending the timeless fedora crown with a glamorous 4...

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    $ 57.00
  • 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
  • Hand Crocheted Raffia Kettle Brim Hat - Rust Kettle Brim Hat Boardwalk Style Hats
    Hand Crocheted Raffia Kettle Brim Hat - Rust Kettle Brim Hat Boardwalk Style Hats WSda739RT Rust Medium (57 cm)

    Hand Crocheted Raffia Kettle Brim Hat - Rust

    $ 52.00

    Handmade raffia hat with up turned brim. Shapeable, 3" wide brim. Ribbon inner band with drawstring. UPF 50+ rated. One size. 100% raffia

    $ 52.00
  • Brown and Grey Two Tone Raffia Sun Hat - Boardwalk Style Hats Wide Brim Sun Hat Boardwalk Style Hats
    Brown and Grey Two Tone Raffia Sun Hat - Boardwalk Style Hats Wide Brim Sun Hat Boardwalk Style Hats
    Sale

    Brown and Grey Two Tone Raffia Sun Hat - Boardwalk Style Hats

    Original Price $ 42.00
    Current Price $ 15.00

    Step into summer style with this exquisite hand-crocheted raffia sun hat, where a sophisticated grey dome meets a luxurious chocolate brown floppy ...

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    Original Price $ 42.00
    Current Price $ 15.00
    Sale
  • Dona Wool Felt Safari Hat with Aztec Band - Scala Hats Safari Hat Scala Hats LF292-BLK Black Medium (57 cm)
    Dona Wool Felt Safari Hat with Aztec Band - Scala Hats Safari Hat Scala Hats LF292-PECAN Taupe Medium (57 cm)

    Dona Wool Felt Safari Hat with Aztec Band - Scala Hats

    $ 69.00

    Explore the timeless appeal of this wool felt safari hat, expertly crafted with a distinctive dented crown and front pinch detail. The generous 3.2...

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    $ 69.00
  • Small Brim Knit Soft Wool Bolero Hat for Women - Adora® Bolero Hat Adora Hats AD1323B Brown M/L (58.5 cm)
    Small Brim Knit Soft Wool Bolero Hat for Women - Adora® Bolero Hat Adora Hats AD1323A Black M/L (58.5 cm)

    Small Brim Knit Soft Wool Bolero Hat for Women - Adora®

    $ 24.00

    This refined soft wool bolero hat epitomizes understated elegance for autumn and winter wear. Featuring a gracefully flat crown with clean sidewall...

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    $ 24.00

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.