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Adjustable Size Hats

  • Victoria by Wallaroo Hats Kettle Brim Hat Wallaroo Hats
    Victoria by Wallaroo Hats Kettle Brim Hat Wallaroo Hats

    Victoria by Wallaroo Hats

    from $ 53.00

    Discover the Victoria by Wallaroo—the go-to hat for women who refuse to compromise on style or comfort. Featuring a chic turned-up Breton brim and ...

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    from $ 53.00
  • Victoria Fedora by Wallaroo Hats Safari Hat Wallaroo Hats
    Victoria Fedora by Wallaroo Hats Safari Hat Wallaroo Hats Sale

    Victoria Fedora by Wallaroo Hats

    Original Price $ 55.00
    from $ 40.00

    The Victoria Fedora blends Wallaroo’s bestselling Victoria construction with a classic fedora crown, creating a stylish everyday sun hat perfect fo...

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    Original Price $ 55.00
    from $ 40.00
    Sale
  • Cotton Up Turned Large Brim Sun Hat - Scala Hats for Women Kettle Brim Hat Scala Hats
    Cotton Up Turned Large Brim Sun Hat - Scala Hats for Women Kettle Brim Hat Scala Hats

    Cotton Up Turned Large Brim Sun Hat - Scala Hats for Women

    $ 36.00

    Shield yourself from the sun with this elegant cotton wide-brim hat from Scala. Featuring a generous 3.5" upturned brim and UPF 50+ protection endo...

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    $ 36.00
  • Cotton Souwestern Summer Hat - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats
    Cotton Souwestern Summer Hat - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats hh1391E Light Blue OS

    Cotton Souwestern Summer Hat - Sun 'N' Sand Hats

    $ 27.00

    Experience effortless style and comfort with this versatile cotton summer hat. The thoughtfully designed three-panel dome crown pairs with a dimens...

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    $ 27.00
  • Upturned Brim Cotton Breton Hat - Milani Hats Kettle Brim Hat Milani Hats
    Upturned Brim Cotton Breton Hat - Milani Hats Kettle Brim Hat Milani Hats WSCT473RD Red M/L (58.5 cm)
    Sale

    Upturned Brim Cotton Breton Hat - Milani Hats

    Original Price $ 20.00
    Current Price $ 15.00

    This iconic turned-up brim hat commands attention with its bold silhouette and practical edge. Crafted from 100% cotton with a striking light blue ...

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    Original Price $ 20.00
    Current Price $ 15.00
    Sale
  • Breton by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats
    Breton by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats

    Breton by Wallaroo Hat Company

    $ 51.00

    The Breton is one of Wallaroo’s signature wide-brim sun hats, beloved for its graceful shape and flattering coverage. The soft, flexible poly-ribbo...

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    $ 51.00
  • Classic Ladies Cotton Up Brim Hat - Sun 'N' Sand Hats Kettle Brim Hat Sun N Sand Hats
    Classic Ladies Cotton Up Brim Hat - Sun 'N' Sand Hats Kettle Brim Hat Sun N Sand Hats

    Classic Ladies Cotton Up Brim Hat - Sun 'N' Sand Hats

    $ 30.00

    Elevate your summer style with this timeless cotton hat from Sun 'N' Sand Hats—a bestseller for good reason. Crafted from breathable cotton with a ...

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    $ 30.00
  • St. Tropez Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats STTR-24-NA Natural / Navy M/L (58 cm)
    St. Tropez Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Sale

    St. Tropez Trilby by Wallaroo Hat Company

    Original Price $ 49.00
    Current Price $ 26.00

    The St. Tropez Trilby features a shorter brim and structured fedora crown, making it a chic option for women and men seeking a compact summer hat. ...

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    Original Price $ 49.00
    Current Price $ 26.00
    Sale
  • Criss Cross Woven Straw Brim Cap - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH3179C Natural M/L (57-59 cm) Hook and Loop Closure
    Criss Cross Woven Straw Brim Cap - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH3179F Navy M/L (57-59 cm) Hook and Loop Closure

    Criss Cross Woven Straw Brim Cap - Sun 'N' Sand Hats

    $ 27.50

    Shield yourself from the sun in style with this versatile straw brim cap featuring an eye-catching crisscross woven band. The generous 3.75" peak d...

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    $ 27.50
  • Straw Up Brim Hat with Chin Cord - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories JS8595BR Brick Medium (57 cm)
    Straw Up Brim Hat with Chin Cord - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories JS8595BN Brown Medium (57 cm)

    Straw Up Brim Hat with Chin Cord - Jeanne Simmons Hats

    $ 34.00

    Defy the elements with this audacious straw hat designed for adventurers who refuse to compromise. Featuring an upturned brim that commands attenti...

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    $ 34.00
  • Lady Jane by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats
    Lady Jane by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats

    Lady Jane by Wallaroo Hat Company

    $ 71.00

    The Lady Jane is adorned with a printed scarf with Jane Seymour's artwork. It is a lovely upturned brim that frames the face beautifully, giving th...

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    $ 71.00
  • Up Turned Brim Classic Sun Hat - Sun 'N' Sand Hats Kettle Brim Hat Sun N Sand Hats
    Up Turned Brim Classic Sun Hat - Sun 'N' Sand Hats Kettle Brim Hat Sun N Sand Hats HH803M Hot Pink Medium (57 cm)

    Up Turned Brim Classic Sun Hat - Sun 'N' Sand Hats

    $ 31.00

    Embrace timeless elegance with this iconic French breton-inspired sun hat, designed for the modern traveler who refuses to compromise on style or p...

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    $ 31.00
  • Cable Knit Cloche - J. Callanan Women's Hats Cloche Callanan Hats
    Cable Knit Cloche - J. Callanan Women's Hats Cloche Callanan Hats LV451-RD Red Medium (57 cm)
    Sale

    Cable Knit Cloche - J. Callanan Women's Hats

    Original Price $ 27.00
    Current Price $ 19.99

    This adorable cable knit cloche from J. Callanan is your new go-to for effortless style! The wool blend construction keeps you warm while the round...

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    Original Price $ 27.00
    Current Price $ 19.99
    Sale
  • 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
  • Wide Brim Bangkok Toyo Sun Hat with Side Feather - Scala Hats Safari Hat Scala Hats
    Wide Brim Bangkok Toyo Sun Hat with Side Feather - Scala Hats Safari Hat Scala Hats LT240-NAT Natural OS

    Wide Brim Bangkok Toyo Sun Hat with Side Feather - Scala Hats

    $ 39.00

    Experience refined sun protection with this Bangkok toyo straw hat, expertly crafted with a distinctive fedora-inspired crown and precision pinch d...

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    $ 39.00
  • Signoria Bao Straw Fedora Hat - Brooklyn Hat Co Fedora Hat Brooklyn Hat
    Signoria Bao Straw Fedora Hat - Brooklyn Hat Co Fedora Hat Brooklyn Hat BKN1570-RED Dark Red M (57 cm)
    Sale

    Signoria Bao Straw Fedora Hat - Brooklyn Hat Co

    Original Price $ 50.00
    Current Price $ 24.99

    Crafted from hand-woven bao straw, this fedora keeps things breezy and light. The crinkled, multi-toned band with a charming side bow adds personal...

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    Original Price $ 50.00
    Current Price $ 24.99
    Sale
  • 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
  • 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
    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
  • Classic Tweed Straw Beach Hat - Sun 'N' Sand Hats Wide Brim Sun Hat Sun N Sand Hats HH2969D Denim OS (57 cm)
    Classic Tweed Straw Beach Hat - Sun 'N' Sand Hats Wide Brim Sun Hat Sun N Sand Hats HH2969F Coral OS (57 cm)

    Classic Tweed Straw Beach Hat - Sun 'N' Sand Hats

    $ 31.00

    Embrace sun-soaked adventures with this timeless straw beach hat, designed for those who refuse to compromise on style or protection. Featuring UPF...

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    $ 31.00
  • Flamingo Trucker Cap - Sun 'N' Sand Hats Cap Sun N Sand Hats HH3416 Flamingo OS

    Flamingo Trucker Cap - Sun 'N' Sand Hats

    $ 22.00

    Rock your bold style with the Flamingo Trucker Cap from Sun 'N' Sand Hats. This eye-catching six-panel design features a vibrant flamingo print on ...

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    $ 22.00
  • Structured Brim Cloche with Big Flower Accent - John Callanan Handmade Hats Cloche Callanan Hats
    Structured Brim Cloche with Big Flower Accent - John Callanan Handmade Hats Cloche Callanan Hats LV424 Burgundy Medium (57 cm)
    Sale

    Structured Brim Cloche with Big Flower Accent - John Callanan Handmade Hats

    Original Price $ 62.00
    Current Price $ 39.00

    Step back in time with this charming 1920s-inspired cloche that brings vintage glamour to any outfit. Featuring a sleek, structured brim that frame...

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    Original Price $ 62.00
    Current Price $ 39.00
    Sale
  • Poms and Beads Trimmed Floppy Safari Hat by Adora® Safari Hat Adora Hats ad862bd Burgundy Medium (57 cm)
    Poms and Beads Trimmed Floppy Safari Hat by Adora® Safari Hat Adora Hats

    Poms and Beads Trimmed Floppy Safari Hat by Adora®

    $ 35.00

    This elegant wool felt safari hat combines timeless style with bohemian charm. The structured fedora crown features a refined front pinch, while ar...

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    $ 35.00

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.