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Men's Hats for Small Heads

  • Quilted LIL'BRIMS - Black Cap Ultra Sport
    Quilted LIL'BRIMS - Black Cap Ultra Sport lbfa1834m Black Medium/Large
    Sale
    $ 33.00
    $ 5.00
    Ultra Sport

    Quilted LIL'BRIMS - Black

    Quilted six panel cap. Up turned curved small bill. 1.75" peak. Button top. Sewn eyelets on each panel. Lil'Brim pin accent. Cotton and elasticized...

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    $ 33.00
    $ 5.00
    Sale
  • No Donut LIL'BRIMS - Black Cap Ultra Sport
    No Donut LIL'BRIMS - Black Cap Ultra Sport
    Sale
    $ 33.00
    $ 5.00
    Ultra Sport

    No Donut LIL'BRIMS - Black

    Black six panel cap. Up turned curved small bill. 1.75" peak. Button top. Sewn eyelets on each panel. Lil'Brim pin accent. Cotton and elasticized i...

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    $ 33.00
    $ 5.00
    Sale
  • Weathered Cotton Cadet Cap - DPC Outdoor Hat Cap Dorfman Hat Co.
    Weathered Cotton Cadet Cap - DPC Outdoor Hat Cap Dorfman Hat Co. MC169-SM Brown Small/Medium
    $ 27.00
    Dorfman Hat Co.

    Weathered Cotton Cadet Cap - DPC Outdoor Hat

    American Holly leather-look weathered cotton military style cap. Low, flat top cap with short, straight side panels. Slightly curved brim. 2.25", w...

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    $ 27.00
  • 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
  • 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
  • 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

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.