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Adjustable Size Hats

  • Sydney - Wallaroo Hats Kettle Brim Hat Wallaroo Hats
    Sydney - Wallaroo Hats Kettle Brim Hat Wallaroo Hats

    Sydney - Wallaroo Hats

    $ 51.00

    The Sydney Sun Hat is one of Wallaroo’s bestselling summer styles thanks to its soft, breathable poly-braid design of matching hues. The flexible 3...

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    $ 51.00
  • Petite Kristy Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Kristy Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Petite Kristy Fedora by Wallaroo Hat Company

    $ 61.00

    The Petite Kristy Fedora delivers the same polished sophistication as the original Kristy—perfectly scaled for smaller head sizes. Its two-tone sty...

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    $ 61.00
  • Kristy Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Kristy Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Kristy Fedora by Wallaroo Hat Company

    $ 61.00

    The Kristy combines the timeless fedora styling with a feminine edge: its shallow crown and front pinch create sophistication, while the vibrant tw...

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    $ 61.00
  • Petite Charlie by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Charlie by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Petite Charlie by Wallaroo Hat Company

    $ 61.00

    The Petite Charlie Fedora offers the same polished, contemporary look as the bestselling Charlie—tailored perfectly for smaller head sizes. The str...

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    $ 61.00
  • Big Brim Sun Hat with Wide Ribbon and Bow - Milani Hats Wide Brim Hat Milani Hats
    Big Brim Sun Hat with Wide Ribbon and Bow - Milani Hats Wide Brim Hat Milani Hats BB0059nt Natural Heather Medium (57 cm)

    Big Brim Sun Hat with Wide Ribbon and Bow - Milani Hats

    $ 25.00

    Protect yourself in style with this award-winning wide-brim sun hat that's earned customer loyalty for two consecutive years. Crafted from premium ...

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    $ 25.00
  • Asymmetrical Brim Summer Hat - Large and XL Size Women's Hats Wide Brim Hat Jeanne Simmons Accessories
    Asymmetrical Brim Summer Hat - Large and XL Size Women's Hats Wide Brim Hat Jeanne Simmons Accessories js8209TN-L Tan Large (59 cm)

    Asymmetrical Brim Summer Hat - Large and XL Size Women's Hats

    $ 34.00

    Step into sun-smart style with this elegant asymmetrical brim hat, thoughtfully designed for larger head sizes. The unique silhouette features a 3....

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    $ 34.00
  • Asymmetrical Brim Summer Hat - Jeanne Simmons Hats Wide Brim Hat Jeanne Simmons Accessories js8209Bt Black tweed Medium (57 cm)
    Asymmetrical Brim Summer Hat - Jeanne Simmons Hats Wide Brim Hat Jeanne Simmons Accessories

    Asymmetrical Brim Summer Hat - Jeanne Simmons Hats

    $ 32.00

    Stand out from the crowd with this chic asymmetrical brim hat that's anything but ordinary. The front flaunts a generous 3.5" brim while the back t...

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    $ 32.00
  • Gabi Ponytail Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Gabi Ponytail Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Gabi Ponytail Fedora by Wallaroo Hat Company

    $ 61.00

    The Gabi Ponytail Fedora is thoughtfully designed for women who want sun protection without sacrificing their favorite hairstyles. A discreet openi...

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    $ 61.00
  • Petite Gabi by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Gabi by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Petite Gabi by Wallaroo Hat Company

    $ 61.00

    The Petite Gabi Ponytail Fedora offers a smart, comfortable solution for women with smaller head sizes who prefer wearing their hair up. A discreet...

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    $ 61.00
  • Charlie Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Charlie Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Charlie Fedora by Wallaroo Hat Company

    $ 61.00

    Designed with a contemporary silhouette, the Charlie Fedora pairs clean lines with effortless comfort. The structured crown and medium brim create ...

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    $ 61.00
  • Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Petite Palm Beach by Wallaroo Hat Company

    $ 65.00

    The Petite Palm Beach Safari Hat delivers packable convenience and classic outdoor style for smaller head sizes. Its crushable construction allows ...

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    $ 65.00
  • Cotton Bucket Hat with Contrast Tie - Scala Collezione Hats Bucket Hat Scala Hats LC455BKWH Black/White Medium (57 cm)
    Cotton Bucket Hat with Contrast Tie - Scala Collezione Hats Bucket Hat Scala Hats

    Cotton Bucket Hat with Contrast Tie - Scala Collezione Hats

    $ 36.00

    Experience versatile sun protection with this sophisticated Scala Collezione cotton bucket hat. The refined design features a contrast-trimmed brim...

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    $ 36.00
  • Carkella Del Mar Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Carkella Del Mar Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Carkella Del Mar Fedora by Wallaroo Hat Company

    $ 61.00

    The Del Mar Fedora combines sleek styling with practical sun protection, making it a favorite on and off the golf course. Its structured crown and ...

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    $ 61.00
  • Palm Beach Carkella by Wallaroo Hats Safari Hat Wallaroo Hats
    Palm Beach Carkella by Wallaroo Hats Safari Hat Wallaroo Hats PLMBCHMBKM Black M/L (59 cm)

    Palm Beach Carkella by Wallaroo Hats

    $ 65.00

    The Palm Beach Safari Hat offers lightweight performance with classic styling, perfect for golf, travel, outdoor adventures, and daily sun protecti...

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    $ 65.00
  • Two-Tone Ribbon and Straw Kettle Brim Hat - JSA Kettle Brim Hat Jeanne Simmons Accessories
    Two-Tone Ribbon and Straw Kettle Brim Hat - JSA Kettle Brim Hat Jeanne Simmons Accessories js9222bk Black Medium (57 cm)
    Sale

    Two-Tone Ribbon and Straw Kettle Brim Hat - JSA

    Original Price $ 42.00
    Current Price $ 27.00

    This refined summer hat combines timeless elegance with practical functionality. Crafted from cream-colored straw braid accented with a two-tone sp...

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    Original Price $ 42.00
    Current Price $ 27.00
    Sale
  • Multi Tone Up Brim Summer Breton - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories js8004BK Black
    Multi Tone Up Brim Summer Breton - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories

    Multi Tone Up Brim Summer Breton - Jeanne Simmons Hats

    $ 28.00

    Dive into summer style with this vibrant multi-tone poly-straw breton that's as fun as it is functional. The upturned brim and dome crown create a ...

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    $ 28.00
  • Linen Trail Hat with Chin Cord - Scala  Women's Hats Wide Brim Hat Scala Hats LC834-BLK Black Small (55 cm)
    Linen Trail Hat with Chin Cord - Scala  Women's Hats Wide Brim Hat Scala Hats

    Linen Trail Hat with Chin Cord - Scala Women's Hats

    $ 39.99

    Crafted from a textured linen weave, this women's trail hat delivers exceptional sun protection with UPF 50+ rating, ideal for outdoor adventures. ...

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    $ 39.99
  • Black and White Sun Hat with Large Straw Bow - DNMC Hats Facesaver Hat Boardwalk Style Hats
    Black and White Sun Hat with Large Straw Bow - DNMC Hats Facesaver Hat Boardwalk Style Hats DA761-BK Black Medium (57 cm)

    Black and White Sun Hat with Large Straw Bow - DNMC Hats

    $ 29.00

    Make a statement with this sophisticated black and white sun hat, designed to keep you protected and polished. The dramatic straw bow and asymmetri...

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    $ 29.00
  • Elegant Wide Brim Straw Hat - Large and Extra-Large Size Safari Hat Jeanne Simmons Accessories
    Elegant Wide Brim Straw Hat - Large and Extra-Large Size Safari Hat Jeanne Simmons Accessories js8001whL White Large (59 cm)

    Elegant Wide Brim Straw Hat - Large and Extra-Large Size

    $ 29.00

    Step into sophistication with this charming wide-brim straw hat, designed for those who love timeless style with a modern twist. Featuring a classi...

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    $ 29.00
  • Charlie Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Charlie Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Charlie Trilby by Wallaroo Hat Company

    $ 57.00

    The Charlie Unisex Trilby offers a timeless shape with a contemporary feel, featuring a structured crown and shorter brim for a refined, easygoing ...

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    $ 57.00
  • Carkella Lauren by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Lauren by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Lauren by Wallaroo Hat Company

    $ 71.00

    The Lauren brings classic safari styling to modern sun protection with its structured crown and wide, flattering brim. Lightweight and breathable, ...

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    $ 71.00
  • Carkella Kerrigan by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Kerrigan by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Kerrigan by Wallaroo Hat Company

    $ 71.00

    The Kerrigan blends the classic safari silhouette with Carkella’s smart magnetic emblem system. The durable woven fabric with contrasting stitching...

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    $ 71.00
  • Margot by Wallaroo Hat Company Wide Brim Hat Wallaroo Hats
    Margot by Wallaroo Hat Company Wide Brim Hat Wallaroo Hats

    Margot by Wallaroo Hat Company

    $ 77.00

    Created in collaboration with Jane Seymour, the Margot showcases elegant design with striking contrast trim that enhances its sweeping downward bri...

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    $ 77.00
  • Two Tone Small Brim Facesaver Hat - Jeanne Simmons Hats Facesaver Hat Jeanne Simmons Accessories
    Two Tone Small Brim Facesaver Hat - Jeanne Simmons Hats Facesaver Hat Jeanne Simmons Accessories js8202gy White / Grey

    Two Tone Small Brim Facesaver Hat - Jeanne Simmons Hats

    $ 25.00

    This facesaver hat delivers sophisticated sun protection with a refined two-tone design. The white dome crown pairs with a contrasting brim accente...

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    $ 25.00

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.