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Adjustable Size Hats

  • 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
  • Up Brim Summer Hat with Chiffon Scarf - Scala Collection Hats Kettle Brim Hat Scala Hats
    Up Brim Summer Hat with Chiffon Scarf - Scala Collection Hats Kettle Brim Hat Scala Hats LP381-COR Coral OS

    Up Brim Summer Hat with Chiffon Scarf - Scala Collection Hats

    $ 32.00

    Elevate your summer style with this sophisticated hat from Scala's curated collection. Featuring a versatile, shapeable brim that transitions from ...

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    $ 32.00
  • Karen Keith Striped Brim Straw Facesaver Hat with Bow Facesaver Hat Great hats by Karen Keith BT29-B Navy
    Karen Keith Striped Brim Straw Facesaver Hat with Bow Facesaver Hat Great hats by Karen Keith BT29-A Black

    Karen Keith Striped Brim Straw Facesaver Hat with Bow

    $ 33.00

    Embrace effortless style with this Karen Keith straw facesaver hat, designed for those who refuse to compromise between fashion and function. The i...

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    $ 33.00
  • Crushable Lifeguard Hat with Chin Strap - Boardwalk Style Lifeguard Hat Boardwalk Style Hats
    Crushable Lifeguard Hat with Chin Strap - Boardwalk Style Lifeguard Hat Boardwalk Style Hats DA1302-OLIVE Olive Large (59cm)

    Crushable Lifeguard Hat with Chin Strap - Boardwalk Style

    $ 35.00

    Shield yourself from intense sun rays with this versatile lifeguard-inspired hat, engineered for those who refuse to compromise on style or protect...

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    $ 35.00
  • 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
  • Straw Sun Hat with Rhinestone Studded Brim - Sun'N'Sand Hats Wide Brim Sun Hat Sun N Sand Hats HH3201A Tan OS
    Straw Sun Hat with Rhinestone Studded Brim - Sun'N'Sand Hats Wide Brim Sun Hat Sun N Sand Hats HH3201B Black OS

    Straw Sun Hat with Rhinestone Studded Brim - Sun'N'Sand Hats

    $ 37.50

    Shine bright while staying protected with this stunning straw sun hat featuring a glamorous rhinestone-studded wide brim. The sparkling narrow band...

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    $ 37.50
  • Stevie by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats
    Stevie by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats

    Stevie by Wallaroo Hat Company

    $ 69.00

    The Stevie hat brings refined travel-worthy style and serious sun protection into one beautifully designed accessory. Crafted from soft poly-straw ...

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    $ 69.00
  • 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
  • Black and Natural Two Tone Crocheted Raffia Sun Hat - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats
    Black and Natural Two Tone Crocheted Raffia Sun Hat - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats
    Sale

    Black and Natural Two Tone Crocheted Raffia Sun Hat - Boardwalk Style

    Original Price $ 42.00
    Current Price $ 15.00

    Crafted by hand using premium raffia, this stunning capeline-style hat combines timeless elegance with practical sun protection. The natural straw ...

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    Original Price $ 42.00
    Current Price $ 15.00
    Sale
  • 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
  • Sterling Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Sterling Safari by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Sterling Safari by Wallaroo Hat Company

    $ 69.00

    The Sterling by Wallaroo delivers classic safari style with a fresh, nautical twist. Featuring a crisp contrast trim and a coordinating striped hat...

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    $ 69.00
  • Microfiber UV Bill Cap with Neck Cape - Juniper Sport Hats Cap MegaCI
    Microfiber UV Bill Cap with Neck Cape - Juniper Sport Hats Cap MegaCI J7001 Natural 54-57 cm

    Microfiber UV Bill Cap with Neck Cape - Juniper Sport Hats

    $ 22.00

    Step into the sun with unstoppable confidence. This premium microfiber cap is engineered for petite frames, featuring a sculpted four-panel crown a...

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    $ 22.00
  • 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
  • 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
  • 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
  • Flex Weave Straw Wide Brim Beach Hat - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats DA1350-NAT Natural Heather OS (57 cm)
    Flex Weave Straw Wide Brim Beach Hat - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats

    Flex Weave Straw Wide Brim Beach Hat - Boardwalk Style

    $ 49.00

    Turn every shoreline stroll into a style moment with this stunning Flex-Weave straw beach hat, designed to elevate your seaside and resort adventur...

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    $ 49.00
  • 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

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.