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Men's Hats for Small Heads

  • 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
  • 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.