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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
  • 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
  • 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
  • Kinsley Bangkok Toyo Fedora for Petites - Sunny Dayz™ Safari Hat Sun N Sand Hats HK463 Ivory Small (54.5 cm)

    Kinsley Bangkok Toyo Fedora for Petites - Sunny Dayz™

    $ 31.00

    Discover effortless elegance with the Kinsley Bangkok Toyo Fedora, thoughtfully designed for petite frames. This striking ivory straw hat features ...

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    $ 31.00
  • 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
  • Everett Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats EVRT-MC-M Mixed Camel M/L (59 cm)
    Everett Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Everett Fedora by Wallaroo Hat Company

    $ 69.00

    Designed specifically for golfers, the Everett brings together classic fedora style and high-performance bamboo fabric to keep you protected and co...

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    $ 69.00
  • Small Size Woven Straw Safari Hat for Women - Sunny Dayz™ Safari Hat Sun N Sand Hats HK483 Ivory Small (54 cm)

    Small Size Woven Straw Safari Hat for Women - Sunny Dayz™

    $ 28.00

    Embrace effortless summer style with this petite-sized woven straw safari hat, designed for those seeking both elegance and practicality. The refin...

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    $ 28.00
  • Montecito by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Montecito by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Montecito by Wallaroo Hat Company

    $ 69.00

    The Montecito Broad-Brimmed Rancher hat offers a coastal-chic look with its soft, woven texture and relaxed brim. This rancher-style wide-brim hat ...

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    $ 69.00
  • Nosara by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Nosara by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Nosara by Wallaroo Hat Company

    $ 81.00

    The Nosara Wide Brim Sun Hat is handcrafted from natural raffia straw for a rich, authentic texture that captures the spirit of island living. Its ...

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    $ 81.00
  • Two Tone UV Blocking Safari Hat - Karen Keith Hats Safari Hat Great hats by Karen Keith BT14-F Toast

    Two Tone UV Blocking Safari Hat - Karen Keith Hats

    $ 30.00

    Elevate your outdoor style with this braided toyo safari hat, designed for both elegance and high-performance sun protection. The tweed toast-color...

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    $ 30.00
  • Knitted Panama Hat with Gold Band - Grey Safari Hat Boardwalk Style Hats WWda3124GY Grey
    Knitted Panama Hat with Gold Band - Grey Safari Hat Boardwalk Style Hats

    Knitted Panama Hat with Gold Band - Grey

    $ 20.00

    Add a touch of urban sophistication to your wardrobe with this downtown-style knit fedora hat. Featuring a classic dented crown with a pinched fron...

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    $ 20.00
  • Wide Brim Gardening Hat with Chin Cord - Sun 'N' Sand Hats Safari Hat Sun N Sand Hats HH2902B Black OS (57 cm)
    Wide Brim Gardening Hat with Chin Cord - Sun 'N' Sand Hats Safari Hat Sun N Sand Hats HH2902A Tan OS (57 cm)

    Wide Brim Gardening Hat with Chin Cord - Sun 'N' Sand Hats

    $ 33.75

    Step into the garden with timeless style and unwavering sun protection. This wide-brim hat showcases a natural straw crown with an elegant dented s...

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    $ 33.75
  • Dona Wool Felt Safari Hat with Aztec Band - Scala Hats Safari Hat Scala Hats LF292-BLK Black Medium (57 cm)
    Dona Wool Felt Safari Hat with Aztec Band - Scala Hats Safari Hat Scala Hats LF292-PECAN Taupe Medium (57 cm)

    Dona Wool Felt Safari Hat with Aztec Band - Scala Hats

    $ 69.00

    Explore the timeless appeal of this wool felt safari hat, expertly crafted with a distinctive dented crown and front pinch detail. The generous 3.2...

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    $ 69.00
  • Suze Two Tone Wide Brim Safari Sun Hat - John Callanan Safari Hat Callanan Hats
    Suze Two Tone Wide Brim Safari Sun Hat - John Callanan Safari Hat Callanan Hats CR367-TAN Tan Medium (57 cm)
    Sale

    Suze Two Tone Wide Brim Safari Sun Hat - John Callanan

    Original Price $ 54.99
    Current Price $ 43.49

    Crafted by legendary British milliner John Callanan, this two-tone safari stunner pairs a naturally-hued straw crown with contrasting brim detailin...

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    Original Price $ 54.99
    Current Price $ 43.49
    Sale
  • Carkella Vivian by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Vivian by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Vivian by Wallaroo Hat Company

    $ 71.00

    The Vivian offers a sophisticated silhouette with its gently upturned brim and structured safari crown. Designed with Carkella’s magnetic emblem sy...

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    $ 71.00
  • Small Brim Knit Soft Wool Bolero Hat for Women - Adora® Bolero Hat Adora Hats AD1323B Brown M/L (58.5 cm)
    Small Brim Knit Soft Wool Bolero Hat for Women - Adora® Bolero Hat Adora Hats AD1323A Black M/L (58.5 cm)

    Small Brim Knit Soft Wool Bolero Hat for Women - Adora®

    $ 24.00

    This refined soft wool bolero hat epitomizes understated elegance for autumn and winter wear. Featuring a gracefully flat crown with clean sidewall...

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    $ 24.00

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.