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Men's Hats for Small Heads

  • 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
  • Pro Golf Flexfit Solid Baseball Cap - Scala Hats for Men Cap Scala Hats bc303aWH White Small/Medium (57 cm)
    Pro Golf Flexfit Solid Baseball Cap - Scala Hats for Men Cap Scala Hats bc303aNV Navy Small/Medium (57 cm)
    $ 14.00
    Scala Hats

    Pro Golf Flexfit Solid Baseball Cap - Scala Hats for Men

    Designed for the discerning golfer, this six-panel baseball cap combines classic styling with modern performance. The spandex-enhanced polyester fa...

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    $ 14.00
  • 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
  • Weathered Cotton Outback Hat, Small to 3XL Size - DPC Headwear Safari Hat Dorfman Hat Co.
    Weathered Cotton Outback Hat, Small to 3XL Size - DPC Headwear Safari Hat Dorfman Hat Co. MC127BNS Brown Small (55 cm)
    from $ 39.99
    Dorfman Hat Co.

    Weathered Cotton Outback Hat, Small to 3XL Size - DPC Headwear

    Aged leather look, weathered cotton hat Shapeable, wired brim allows to style it as a cowboy or safari style.  Bound 2.75" wide brim. Teardrop crow...

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    from $ 39.99
  • 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
  • DPC Floating Sailing Hat Bucket Hat Dorfman Hat Co.
    DPC Floating Sailing Hat Bucket Hat Dorfman Hat Co. 943-PACK1 Ivory Small (55 cm)
    Sale
    Original Price $ 39.00
    Current Price $ 35.00
    Dorfman Hat Co.

    DPC Floating Sailing Hat

    The DPC Floating Sailing Hat features a classic design crafted from Scotchgard-treated canvas. It offers a 3" flat brim with a green underbrim to r...

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    Original Price $ 39.00
    Current Price $ 35.00
    Sale
  • 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.