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Men's Hats for Small Heads

  • 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
  • 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
  • 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.