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Adjustable Size Hats

  • Tweed Straw Safari Hat - Jeanne Simmons Hats Safari Hat Jeanne Simmons Accessories
    Tweed Straw Safari Hat - Jeanne Simmons Hats Safari Hat Jeanne Simmons Accessories js8250wh White tweed

    Tweed Straw Safari Hat - Jeanne Simmons Hats

    $ 31.00

    Step out in style with this charming tweed straw safari hat from Jeanne Simmons. Crafted from a soft straw and poly blend, it features a classic fe...

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    $ 31.00
  • Tahiti Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats
    Tahiti Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats

    Tahiti Cowboy by Wallaroo Hat Company

    $ 71.00

    The Tahiti Cowboy Hat brings tropical Western style to summer outfits with its hand-crocheted raffia construction and sculpted cowboy crown accente...

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    $ 71.00
  • Petite Catalina Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats
    Petite Catalina Cowboy by Wallaroo Hat Company Cowboy Hat Wallaroo Hats

    Petite Catalina Cowboy by Wallaroo Hat Company

    $ 69.00

    The Petite Catalina Cowboy Hat brings classic Western styling to smaller head sizes, offering a flattering silhouette with breezy warm-weather comf...

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    $ 69.00
  • Caroline Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Caroline Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Caroline Fedora by Wallaroo Hat Company

    $ 61.00

    The Caroline Fedora blends timeless styling with lightweight wearability, making it a versatile choice for sunny days. Its refined pinch-front crow...

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    $ 61.00
  • Karen Keith Poly Braid Facesaver Hat Facesaver Hat Great hats by Karen Keith
    Karen Keith Poly Braid Facesaver Hat Facesaver Hat Great hats by Karen Keith P9cbBN Brown

    Karen Keith Poly Braid Facesaver Hat

    $ 28.00

    Unleash your potential with this ingeniously designed facesaver hat—your passport to sun-soaked confidence. The distinctive backless construction p...

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    $ 28.00
  • 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
  • Downturned Big Brim Asymmetrical Summer Hat Wide Brim Hat JEL WSPS608BG Natural tweed
    Downturned Big Brim Asymmetrical Summer Hat Wide Brim Hat JEL WSPS608BN Brown tweed

    Downturned Big Brim Asymmetrical Summer Hat

    $ 25.00

    Packable straw hat with grosgrain ribbon bow. Asymmetrical brim, 4" wide on front and narrows to 2" towards back. Adjustable drawstring inside. Gre...

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    $ 25.00
  • Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats LT209-TOA Toast
    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats

    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats

    $ 36.99

    Escape the sun in style with this stunning Bangkok toyo straw floppy hat from Scala Hats. The distinctive split-back design accommodates low ponyta...

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    $ 36.99
  • 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
  • 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
  • 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
  • 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
  • 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
  • Unisex Gardening Hat with Chin Cord - Large and XL Sizes Safari Hat Jeanne Simmons Accessories js6962l Brown Large (59 cm)
    Unisex Gardening Hat with Chin Cord - Large and XL Sizes Safari Hat Jeanne Simmons Accessories

    Unisex Gardening Hat with Chin Cord - Large and XL Sizes

    $ 27.00

    Shield yourself from the sun with this versatile gardening hat, designed for both men and women who demand protection without compromise. The gener...

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    $ 27.00
  • 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
  • Carkella Sydney Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats SYDFM-DM Denim M/L (58 cm)
    Carkella Sydney Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Sydney Fedora by Wallaroo Hat Company

    $ 51.00

    The Sydney Fedora blends contemporary styling with Carkella’s signature magnetic emblem feature—allowing you to customize your hat with interchange...

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    $ 51.00
  • Open Crown Straw Sun Visor Hat - Boardwalk Hats Visor Cap Boardwalk Style Hats
    Open Crown Straw Sun Visor Hat - Boardwalk Hats Visor Cap Boardwalk Style Hats

    Open Crown Straw Sun Visor Hat - Boardwalk Hats

    $ 25.00

    Stay stylish and protected with this women’s heathered straw sun visor, designed for comfortable, flattering coverage all season long. The wide 4" ...

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    $ 25.00
  • Plaid Fedora with Button Accent for Fall - Adora Hats® Fedora Hat Adora Hats AD1200A Camel S/M (56-57 cm)

    Plaid Fedora with Button Accent for Fall - Adora Hats®

    $ 21.00

    This refined plaid trilby from Adora Hats® combines timeless elegance with thoughtful design details. Constructed in a sophisticated light-to-dark ...

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    $ 21.00
  • 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
  • Summer Floppy Hat with Linen Scarf by Milani Floppy Hat Milani Hats
    Summer Floppy Hat with Linen Scarf by Milani Floppy Hat Milani Hats BB0058LT Latte

    Summer Floppy Hat with Linen Scarf by Milani

    $ 25.00

    Stay sun-safe in style with this charming floppy hat from Milani. The generous 5-inch brim keeps rays at bay while the UPF 50+ protection works ove...

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    $ 25.00
  • Little Bucket Hat with Split Brim - Jeanne Simmons Hats Cloche Jeanne Simmons Accessories
    Little Bucket Hat with Split Brim - Jeanne Simmons Hats Cloche Jeanne Simmons Accessories JS9160 Brown

    Little Bucket Hat with Split Brim - Jeanne Simmons Hats

    $ 20.00

    This standout women’s packable sun hat was designed for effortless summer style. The 2.5" shapeable brim lets you customize your look—tilt it, curv...

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    $ 20.00

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.