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Men's Hats for Small Heads

  • Small Heads Pigment Dyed Garment Washed Twill Bucket Hat - DPC Bucket Hat Dorfman Hat Co. C835 Sand Jr. S/M (53-54 cm)
    Small Heads Pigment Dyed Garment Washed Twill Bucket Hat - DPC Bucket Hat Dorfman Hat Co. C835 Stone Jr. S/M (53-54 cm)
    $ 13.50
    Dorfman Hat Co.

    Small Heads Pigment Dyed Garment Washed Twill Bucket Hat - DPC

    Traditional cotton bucket hat for small head sizes. Pigment dyed garment washed twill. 2" wide stitched, bound brim. Two metal eyelets on both side...

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    $ 13.50
  • Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons
    Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons js1239-TAN Tan XS (55 cm)
    $ 24.00
    Jeanne Simmons

    Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats

    Meet your new favorite travel companion! This charming paper braid fedora is designed specifically for smaller heads and brings instant personality...

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    $ 24.00
  • Fine Braid Safari Hat with Black Band - Scala Hats for Men Safari Hat Scala Hats
    Fine Braid Safari Hat with Black Band - Scala Hats for Men Safari Hat Scala Hats ms449m Natural Small/Medium (56-57 cm)
    $ 28.50
    Scala Hats

    Fine Braid Safari Hat with Black Band - Scala Hats for Men

    This men's safari hat from Scala combines timeless design with practical performance features. Constructed from fine paper braid, it offers UPF 50+...

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    $ 28.50
  • Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Petite Sedona by Wallaroo Hat Company

    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
  • Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    $ 33.00
    Wallaroo Hats

    Jr. Explorer by Wallaroo Hats

    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
  • Waxed Canvas Casual Safari Hat - Texas Gold Hats Safari Hat Texas Gold Hats
    Waxed Canvas Casual Safari Hat - Texas Gold Hats Safari Hat Texas Gold Hats jr7017 Ivory Small (56 cm)
    $ 19.00
    Texas Gold Hats

    Waxed Canvas Casual Safari Hat - Texas Gold Hats

    Stiff waxed canvas men's safari hat. Dented crown with side pinch. Vented mid-crown. Leather band with contrast color twisted overlay. Elastic comf...

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    $ 19.00
  • 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
    $ 17.00
    Dorfman Hat Co.

    Unisex Boonie with Contrast Under Brim - St. Johns Bay

    Feather weight Taslon fishing bucket hat. Contrast trim and under-brim. Metal eyelets. Toggle sizing band. 2.5" wide soft brim. UPF 50+ sun protect...

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    $ 17.00
  • Brushed Twill Mesh Crown Safari with Chin Cord - DPC Outdoor Design Safari Hat Dorfman Hat Co.
    Brushed Twill Mesh Crown Safari with Chin Cord - DPC Outdoor Design Safari Hat Dorfman Hat Co. 864M-KAKI1 Khaki Small (55 cm)
    $ 39.50
    Dorfman Hat Co.

    Brushed Twill Mesh Crown Safari with Chin Cord - DPC Outdoor Design

    Lightweight, airy safari hat provides excellent sun protection. Dented crown with mesh sidewall.  Slightly downward sloping brim, 3" wide. Chin cor...

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    $ 39.50
  • Stetson Hats Mesh Outback Hat for Men up to 2XL - Natural Safari Hat Stetson Hats STC205-NAT1 Natural Small
    $ 51.99
    Stetson Hats

    Stetson Hats Mesh Outback Hat for Men up to 2XL - Natural

    Outback style breezy mesh hat. Nylon mesh construction makes this hat tough enough to take along for all your wet of dry outdoor adventures. Covere...

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    $ 51.99
  • Adventurer Low Profile Safari Hat - Henschel Hats Safari Hat Henschel Hats H5316-KHS Khaki Small (22")
    Adventurer Low Profile Safari Hat - Henschel Hats Safari Hat Henschel Hats H5316-EAS Earth Small (22")
    $ 47.00
    Henschel Hats

    Adventurer Low Profile Safari Hat - Henschel Hats

    Packable lightweight hat for all adventurers. Flat low rise cotton crown top, sloping toward back. Mesh side panels to maximize airflow. Cotton bri...

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    $ 47.00
  • Mesh Outback Hat for Men up to 2XL, Clay - Stetson and Scala Hats Safari Hat Stetson Hats SC205-CLAY3 Clay Scala Hats Large
    Mesh Outback Hat for Men up to 2XL, Clay - Stetson and Scala Hats Safari Hat Stetson Hats STC205-CLAY1 Clay Stetson Hats Small
    $ 51.00
    Stetson Hats

    Mesh Outback Hat for Men up to 2XL, Clay - Stetson and Scala Hats

    Legendary Stetson® Hats for men. Grand Canyon breezy mesh crown safari hat. Nylon mesh construction makes this hat tough enough to take along for a...

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    $ 51.00
  • Solarweave® Cotton Boonie - DPC Outdoor Design Bucket Hat Dorfman Hat Co.
    Solarweave® Cotton Boonie - DPC Outdoor Design Bucket Hat Dorfman Hat Co. SPF1S Oatmeal Small (55 cm)
    $ 23.00
    Dorfman Hat Co.

    Solarweave® Cotton Boonie - DPC Outdoor Design

    Lightweight, comfortable brushed cotton boonie. Flat crown with side snaps and double eyelets. Stitched, bound brim with covered underbrim, 3" wide...

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    $ 23.00
  • Head 'N Home Cabana Sand SolAir Breathable Mesh Shade Hat S to 2XL Safari Hat Head'N'Home Hats
    Head 'N Home Cabana Sand SolAir Breathable Mesh Shade Hat S to 2XL Safari Hat Head'N'Home Hats CabanaSDS Sand S (55 cm - 6 7/8)
    $ 97.00
    Head'N'Home Hats

    Head 'N Home Cabana Sand SolAir Breathable Mesh Shade Hat S to 2XL

    Escape the heat in style with this ultra-light outback hat that's ready for adventure. Crafted from durable nylon and polyester, it crushes down fo...

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    $ 97.00
  • Garment Washed Twill Boonie Hat with Hibiscus Print by MCI Caps Bucket Hat MegaCI 7915bds Wine Small (56 cm)
    Garment Washed Twill Boonie Hat with Hibiscus Print by MCI Caps Bucket Hat MegaCI 7915nxs Navy Small (56 cm)
    $ 16.00
    MegaCI

    Garment Washed Twill Boonie Hat with Hibiscus Print by MCI Caps

    Khaki wide brim bucket hat, boonie with assorted color hibiscus print bands. Stitched, 3" wide brim with matching color underbrim. Sewn ventilation...

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    $ 16.00
  • Aussie Packable Breezer, S to 3XL Hat Sizes - Henschel Hats Safari Hat Henschel Hats h5310NTS Natural Small (21 1/2")
    Aussie Packable Breezer, S to 3XL Hat Sizes - Henschel Hats Safari Hat Henschel Hats h5310OLS Green Small (21 1/2")
    $ 50.00
    Henschel Hats

    Aussie Packable Breezer, S to 3XL Hat Sizes - Henschel Hats

    Packable Aussie outback breezer hat. Cotton crown top, slightly dented center. Mesh side panels. Cotton brim with soft mesh overlay, 3" wide. Soft ...

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    $ 50.00
  • Henschel Hats - Side Snap Aussie Sun Hat Safari Hat Henschel Hats H5336KHS Khaki Small (21 1/2")
    Henschel Hats - Side Snap Aussie Sun Hat Safari Hat Henschel Hats H5336OLS Olive Small (21 1/2")
    Sale
    Original Price $ 51.00
    from $ 39.00
    Henschel Hats

    Henschel Hats - Side Snap Aussie Sun Hat

    Cotton twill Aussie outback hat with side snaps from small to 3XL hat sizes. Solid, slightly dented crown top for excellent sun protection. Left si...

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    Original Price $ 51.00
    from $ 39.00
    Sale
  • Packable Hiker Hat, S to 3XL Hat Sizes - Henschel Breezer Hats Safari Hat Henschel Hats h4310BKM Black Medium (22 1/4")
    Packable Hiker Hat, S to 3XL Hat Sizes - Henschel Breezer Hats Safari Hat Henschel Hats h4310eaS Earth Small (21 1/2")
    $ 49.00
    Henschel Hats

    Packable Hiker Hat, S to 3XL Hat Sizes - Henschel Breezer Hats

    Crushable soft mesh breezer hat. Solid, dented crown top for excellent sun protection. Mesh side panel. Soft mesh covered, 2.5" wide, bound brim. S...

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    $ 49.00
  • Hiker Low Crown Safari Breezer Hat - Henschel Hats Safari Hat Henschel Hats h5196KHM Khaki Medium (22 1/4")
    Hiker Low Crown Safari Breezer Hat - Henschel Hats Safari Hat Henschel Hats h5196KHS Khaki Small (22")
    $ 47.00
    Henschel Hats

    Hiker Low Crown Safari Breezer Hat - Henschel Hats

    Low C-crown safari hat. Mesh breezer side panel. Cotton bound brim, 2.5" wide. Cotton crown top for excellent sun protection. Soft inner sweatband....

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    $ 47.00
  • 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)
    $ 16.50
    Great hats by Karen Keith

    Cotton Bucket Hat with Drawstring - Karen Keith Hats

    Traditional cotton bucket hat for men and women. Narrow brim, 2.5" wide with stitching detail. Square crown, 4" deep. Inner drawstring to reduce si...

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    $ 16.50
  • Reversible Cotton Bucket Hat - Karen Keith Hats Bucket Hat Great hats by Karen Keith
    Reversible Cotton Bucket Hat - Karen Keith Hats Bucket Hat Great hats by Karen Keith MSch15OLM Olive S/M (55-56 cm)
    $ 16.50
    Great hats by Karen Keith

    Reversible Cotton Bucket Hat - Karen Keith Hats

    Classic cotton bucket hat for men and women. Stitched brim, 2.5" wide. Square crown, 4" deep. Reversible. Shapeable brim. 100% cotton.

    $ 16.50
  • DPC Global Packable Bucket Hat with Snap Brim Bucket Hat Dorfman Hat Co.
    DPC Global Packable Bucket Hat with Snap Brim Bucket Hat Dorfman Hat Co. 830HS-KAKI2 Khaki Medium (57 cm)
    $ 15.99
    Dorfman Hat Co.

    DPC Global Packable Bucket Hat with Snap Brim

    Classic poplin bucket hat. Oval sunken crown top. Slightly tapering sidewalls. Shapeable 1.75" wide bound brim. Sewn eyelets. Two tone contrast col...

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    $ 15.99
  • Traditional Summer Fedora Hat - Small to XLarge Hat Sizes Fedora Hat Jeanne Simmons
    Traditional Summer Fedora Hat - Small to XLarge Hat Sizes Fedora Hat Jeanne Simmons js6759ivs Ivory S (56cm)
    $ 21.00
    Jeanne Simmons

    Traditional Summer Fedora Hat - Small to XLarge Hat Sizes

    Experience timeless style with this beloved straw fedora, expertly proportioned for smaller head sizes. Featuring a gracefully pinched crown and na...

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    $ 21.00
  • 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
    Original Price $ 18.00
    Current Price $ 12.99
    Milani Hats

    Large Bill Flap Cap - Milani Hats

    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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    Original Price $ 18.00
    Current Price $ 12.99
    Sale

A great hat should look sharp and feel effortless—and that starts with the right size. Our collection of men’s hats for small head sizes is curated specifically for a secure, comfortable fit in Small (55–56 cm / 21 7/8–22"), so you don’t have to settle for hats that ride too low, slip, or feel bulky.

Shop small men’s hats in a wide variety of classic silhouettes, including small men’s fedora hats, porkpie hats, and winter-ready flat caps for timeless cold-weather style. For warm-weather performance and outdoor comfort, explore mesh-side safari and outback hats sized for smaller heads—designed to deliver breathable airflow and reliable sun coverage for travel, golf, hiking, and everyday outdoor wear. The result: better fit, better shape, and a hat that looks like it was made for you.