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Adjustable Size Hats

  • Large Bill Flap Cap - Milani Hats Cap Milani Hats
    Large Bill Flap Cap - Milani Hats Cap Milani Hats F006-NG Neon Green OS (56-60 cm) Sale

    Large Bill Flap Cap - Milani Hats

    $ 18.00
    $ 12.99

    This bold four-panel cap commands attention with its oversized 2.75" bill and protective neck flap that shields you from sun exposure. Engineered f...

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    $ 18.00
    $ 12.99
    Sale
  • Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Petite Sedona by Wallaroo Hat Company

    $ 61.00

    The Petite Sedona brings rustic charm and sun-smart performance to smaller head sizes. Its woven paper-braid texture offers breathable comfort, whi...

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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
  • Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats Bucket Hat Dorfman Hat Co.
    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats Bucket Hat Dorfman Hat Co. MC2-KAKI1 Khaki Small (55 cm)

    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats

    $ 26.99

    Built for hiking, fishing, travel, and outdoor adventures, the Trailer Boonie Hat by DPC Outdoor combines advanced performance features with all-da...

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    $ 26.99
  • Avery Wide Brim Golf Hat - Wallaroo Hats Fedora Hat Wallaroo Hats
    Avery Wide Brim Golf Hat - Wallaroo Hats Fedora Hat Wallaroo Hats

    Avery Wide Brim Golf Hat - Wallaroo Hats

    $ 69.00

    The Avery brings a contemporary twist to the classic fedora silhouette. Made with lightweight, breathable materials, it’s an easy choice for warm-w...

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    $ 69.00
  • Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK455 Natural / Pink Small (54 cm)
    Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK454 Tan / Blue Small (54 cm)

    Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats

    $ 28.75

    Embrace your unique style with this petite fedora, expertly crafted for smaller head sizes. Featuring a distinctive tribal-patterned woven band and...

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    $ 28.75
  • Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. mc288whs White S/M (57 cm)

    Supplex Dimensional Brim Hat, White - DPC Outdoor Headwear

    $ 33.00

    Experience the perfect blend of performance and comfort with this Supplex Dimensional Brim Hat. Crafted from innovative Supplex® fabric, it deliver...

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    $ 33.00
  • 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
  • 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
  • Supplex Dimensional Brim Hat, Grey - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, Grey - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC288-GREY1 Grey S/M

    Supplex Dimensional Brim Hat, Grey - DPC Outdoor Headwear

    $ 32.00

    Embrace adventure with confidence in this DPC Outdoor boonie-style hat, engineered for serious explorers. The dimensional brim spans 4" front and b...

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    $ 32.00
  • Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats

    Jr. Explorer by Wallaroo Hats

    $ 33.00

    The JR. Explorer Hat is built for active kids and petite adults who love exploring outside. Made from lightweight, breathable microfiber, it offers...

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    $ 33.00
  • Unisex Boonie with Contrast Under Brim - St. Johns Bay Bucket Hat Dorfman Hat Co.
    Unisex Boonie with Contrast Under Brim - St. Johns Bay Bucket Hat Dorfman Hat Co. jcpbh196s Army Small/Medium

    Unisex Boonie with Contrast Under Brim - St. Johns Bay

    $ 17.00

    Embrace adventure with this ultralight Taslon boonie hat, engineered for explorers. The contrast under-brim and trim add distinctive style, while m...

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    $ 17.00
  • Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons Accessories
    Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons Accessories JS8439BZ Bronze Small (56 cm)

    Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats

    $ 24.00

    Discover timeless summer style with this petite straw fedora, expertly crafted for smaller head sizes. The soft paper braid construction offers bre...

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    $ 24.00
  • Supplex Dimensional Brim Hat, Slate - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC288SLATE1 Slate S/M (56 cm)
    Supplex Dimensional Brim Hat, Slate - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.

    Supplex Dimensional Brim Hat, Slate - DPC Outdoor Headwear

    $ 32.00

    Step into the outdoors with unwavering confidence wearing this Supplex Dimensional Brim Hat. Crafted from premium Supplex® nylon, this hat combines...

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    $ 32.00
  • Carkella Portland by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Portland by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Portland by Wallaroo Hat Company

    $ 69.00

    The Portland Golf Hat is engineered for sun protection and all-day comfort on the course. Its structured safari crown and wide brim offer maximum s...

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    $ 69.00
  • Tommy Bahama Performance Flap Cap with Sun Shield Cap Tommy Bahama Hats TBW276-NAVY1 Navy S/M
    Tommy Bahama Performance Flap Cap with Sun Shield Cap Tommy Bahama Hats TBW276-KAKI1 Khaki S/M

    Tommy Bahama Performance Flap Cap with Sun Shield

    $ 29.00

    Take on sunny days with confidence in this Tommy Bahama Performance Fabric Flap Cap, engineered for superior coverage and all-day comfort. Crafted ...

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    $ 29.00
  • Taslon Large Bill UV Cap with Neck Cape - Juniper UV Wear Cap MegaCI
    Taslon Large Bill UV Cap with Neck Cape - Juniper UV Wear Cap MegaCI J7250-WHT White

    Taslon Large Bill UV Cap with Neck Cape - Juniper UV Wear

    $ 29.75

    Embrace sun protection without compromise. This expansive UV cap features a commanding 180-degree brim with a 4.25" peak, paired with an innovative...

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    $ 29.75
  • Supplex Dimensional Brim Hat, Fossil - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Supplex Dimensional Brim Hat, Fossil - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. mc288fss Fossil S/M (56 - 58 cm)

    Supplex Dimensional Brim Hat, Fossil - DPC Outdoor Headwear

    $ 32.00

    Embrace adventure with confidence in the Supplex Dimensional Brim Hat. This boonie-style design features a generously proportioned brim—4" front an...

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    $ 32.00
  • 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
  • Cooling Dimensional Brim Hiking Hat, Chin Strap - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.
    Cooling Dimensional Brim Hiking Hat, Chin Strap - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC416-KAKI2 Khaki Labeled: S/M; Actual size: 55.5 cm (S)
    Sale

    Cooling Dimensional Brim Hiking Hat, Chin Strap - DPC Outdoor Headwear

    $ 40.00
    $ 20.00

    Take on hot, sunny days with confidence in this nylon blend camp hat featuring advanced HyperKewl™ cooling technology. Designed for high-performanc...

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    $ 40.00
    $ 20.00
    Sale

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.