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Adjustable Size Hats

  • Tahiti Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Tahiti Fedora by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Tahiti Fedora by Wallaroo Hat Company

    $ 67.00

    The Tahiti Fedora offers natural island-inspired beauty with its hand-crocheted raffia construction and lightweight, breathable feel. The narrow br...

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    $ 67.00
  • Cotton Bucket Hat with Drawstring - Karen Keith Hats Bucket Hat Great hats by Karen Keith
    Cotton Bucket Hat with Drawstring - Karen Keith Hats Bucket Hat Great hats by Karen Keith ch50OLM Olive S/M (54-56 cm)

    Cotton Bucket Hat with Drawstring - Karen Keith Hats

    $ 16.50

    Elevate your everyday with this iconic cotton bucket hat, crafted for those who refuse to compromise on style or substance. Featuring a refined 2.5...

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    $ 16.50
  • Logan Unisex Safari Hat - Wallaroo Hats Safari Hat Wallaroo Hats
    Logan Unisex Safari Hat - Wallaroo Hats Safari Hat Wallaroo Hats

    Logan Unisex Safari Hat - Wallaroo Hats

    $ 61.00

    The Logan Safari Hat delivers durable performance with a relaxed, masculine profile. Its wide brim provides comfortable shade, while breathable fab...

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    $ 61.00
  • Small Kettle Brim Summer Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories
    Small Kettle Brim Summer Hat - Jeanne Simmons Hats Kettle Brim Hat Jeanne Simmons Accessories js8329bk Black OS (57 cm)

    Small Kettle Brim Summer Hat - Jeanne Simmons Hats

    $ 29.00

    Discover effortless sun protection with this charming kettle brim summer hat from Jeanne Simmons. The distinctive upturned brim and dome crown crea...

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    $ 29.00
  • Asymmetrical Big Brim Summer Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Asymmetrical Big Brim Summer Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA221-1 TT Toast tweed Medium (57 cm)

    Asymmetrical Big Brim Summer Hat - Boardwalk Style

    $ 31.00

    Discover effortless sun protection with this sophisticated asymmetrical design. The generous 4-inch front brim tapers gracefully to 3 inches at the...

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    $ 31.00
  • Bangkok Toyo Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats
    Bangkok Toyo Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats LT171BL Black

    Bangkok Toyo Summer Floppy Hat - Scala Hats

    $ 36.99

    Escape to tropical elegance with this stunning Bangkok toyo straw floppy hat from Scala Hats. Featuring a graceful dome crown and an expansive 5-in...

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    $ 36.99
  • Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. mc288khs Khaki S/M

    Supplex Dimensional Brim Hat, Khaki - DPC Outdoor Headwear

    $ 32.00

    Conquer every outdoor challenge with a hat designed for those who refuse to compromise. Built from premium Supplex® fabric, this boonie-style hat d...

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    $ 32.00
  • Petite Marseille by Wallaroo Hat Company Wide Brim Hat Wallaroo Hats
    Petite Marseille by Wallaroo Hat Company Wide Brim Hat Wallaroo Hats

    Petite Marseille by Wallaroo Hat Company

    $ 73.00

    The Petite Marseille brings Wallaroo’s iconic designer striped wide-brim style to smaller head sizes. Its dramatic downward-curved brim offers exce...

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    $ 73.00
  • 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
  • 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
  • Ribbon Sun Hat with Flower Button - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Ribbon Sun Hat with Flower Button - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA773-BG White Medium (57 cm)

    Ribbon Sun Hat with Flower Button - Boardwalk Style

    $ 25.00

    Shield yourself from the sun in style with this charming ribbon sun hat featuring an elegant wooden flower button accent. The shapeable medium-wide...

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    $ 25.00
  • Taslon Folding-Bill Canyon Cap with Sun Shield - Juniper Hat Cap MegaCI
    Taslon Folding-Bill Canyon Cap with Sun Shield - Juniper Hat Cap MegaCI J7236 Khaki

    Taslon Folding-Bill Canyon Cap with Sun Shield - Juniper Hat

    $ 26.00

    Engineered for the adventurer who refuses to compromise, this Taslon cap transforms your outdoor experience with innovative design and protective p...

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    $ 26.00
  • Metallic Straw Safari Hat with Chin Cord - Sun 'N' Sand Hats Safari Hat Sun N Sand Hats HH2372A Tan / Gold Medium (57 cm)
    Metallic Straw Safari Hat with Chin Cord - Sun 'N' Sand Hats Safari Hat Sun N Sand Hats HH2372C White / Silver Medium (57 cm)

    Metallic Straw Safari Hat with Chin Cord - Sun 'N' Sand Hats

    $ 40.50

    Embrace the sun with confidence in this striking metallic safari hat designed for the modern woman. The shimmering thread catches the light beautif...

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    $ 40.50
  • 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
  • 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
  • Packable, Washable Split Brim Straw Sun Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Packable, Washable Split Brim Straw Sun Hat - Boardwalk Style Wide Brim Hat Boardwalk Style Hats DA1864-NAT Natural/Tan OS (57 cm)

    Packable, Washable Split Brim Straw Sun Hat - Boardwalk Style

    $ 31.00

    Experience the ideal balance of elegance and functionality with this charming straw sun hat, designed for effortless boardwalk style and reliable s...

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    $ 31.00
  • Navy Ribbon Trimmed Ivory Straw Summer Hat - Karen Keith Wide Brim Hat Great hats by Karen Keith
    Navy Ribbon Trimmed Ivory Straw Summer Hat - Karen Keith Wide Brim Hat Great hats by Karen Keith BT17-NAVY Ivory / Navy OS (57 cm)

    Navy Ribbon Trimmed Ivory Straw Summer Hat - Karen Keith

    $ 33.00

    Embrace sun-soaked days in effortless sophistication with this elegant women’s wide-brim straw hat. Designed with a graceful dome crown and a beaut...

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    $ 33.00
  • Two Tone Backless Facesaver Sun Hat - Jeanne Simmons Facesaver Hat Jeanne Simmons Accessories
    Two Tone Backless Facesaver Sun Hat - Jeanne Simmons Facesaver Hat Jeanne Simmons Accessories JS8331-BKWT Black/Wheat

    Two Tone Backless Facesaver Sun Hat - Jeanne Simmons

    $ 32.00

    Meet the ultimate sunny day solution for women who want maximum face coverage: this two-tone backless facesaver sun hat delivers polished style and...

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    $ 32.00
  • Woven Bangkok Straw Sun Hat with Split Brim - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats
    Woven Bangkok Straw Sun Hat with Split Brim - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats DA767-NTbk Natural Medium (57 cm)

    Woven Bangkok Straw Sun Hat with Split Brim - Boardwalk Style

    $ 29.00

    This versatile straw sun hat combines style and function with its distinctive split brim design—ideal for keeping your ponytail free while staying ...

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    $ 29.00
  • Santiago Small Size Straw Safari Hat - Sunny Dayz™ Safari Hat Sun N Sand Hats HK489 Natural Small (54 cm)

    Santiago Small Size Straw Safari Hat - Sunny Dayz™

    $ 28.00

    Discover the perfect fit with this petite Panama-style safari hat, expertly crafted for smaller head sizes. The artfully dented crown and classic p...

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    $ 28.00
  • Heather Floppy Sun Hat with Chin Strap - Milani Hats Wide Brim Sun Hat Milani Hats
    Heather Floppy Sun Hat with Chin Strap - Milani Hats Wide Brim Sun Hat Milani Hats BB005nt Natural Heather Medium (57 cm)

    Heather Floppy Sun Hat with Chin Strap - Milani Hats

    $ 26.00

    Stay shaded in style with this charming heather floppy sun hat from Milani. Crafted from soft toyo braid, it features a generous 4.5" brim perfect ...

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    $ 26.00

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.