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Men's Hats for Small Heads

  • Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Petite Palm Beach by Wallaroo Hat Company

    $ 65.00

    The Petite Palm Beach Safari Hat delivers packable convenience and classic outdoor style for smaller head sizes. Its crushable construction allows ...

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    $ 65.00
  • Pro Style Twill Cap for Small Heads - MCI Hats Cap MegaCI
    Pro Style Twill Cap for Small Heads - MCI Hats Cap MegaCI 6901BY-LGY Light Grey 51-55 cm

    Pro Style Twill Cap for Small Heads - MCI Hats

    $ 7.50

    Petite Baseball Cap for Small Heads This petite low-profile baseball cap is the perfect choice for anyone with a smaller head size looking for a st...

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    $ 7.50
  • The Airflo® Tilley Hat - Medium Brim LTM5 Boonie Bucket Hat Tilley Endurables Hats
    The Airflo® Tilley Hat - Medium Brim LTM5 Boonie Bucket Hat Tilley Endurables Hats H00HT1005728101 Rockface 6 7/8 (55 cm)

    The Airflo® Tilley Hat - Medium Brim LTM5 Boonie

    $ 99.00

    The best-selling classic Tilley hat is a trusted choice for rain or shine, designed to perform wherever your day takes you. This lightweight, unise...

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    $ 99.00
  • The Airflo® Tilley Hat - Broad Brim LTM6 Boonie Bucket Hat Tilley Endurables Hats
    The Airflo® Tilley Hat - Broad Brim LTM6 Boonie Bucket Hat Tilley Endurables Hats H99HT1006493101 KhakiOlive 6 7/8 (55 cm)

    The Airflo® Tilley Hat - Broad Brim LTM6 Boonie

    $ 99.00

    The best-selling classic Tilley hat is a proven favorite for dependable protection in rain or sunshine. Designed in a lightweight, unisex boonie st...

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    $ 99.00
  • Modern Airflo® Boonie Hat - Tilley Hats Bucket Hat Tilley Endurables Hats
    Modern Airflo® Boonie Hat - Tilley Hats Bucket Hat Tilley Endurables Hats H04HT10016102 Light Stone 7 (56 cm)

    Modern Airflo® Boonie Hat - Tilley Hats

    $ 99.00

    Often described as the finest outdoor hat in the world, this lightweight, unisex boonie-style hat is built for serious adventurers and everyday out...

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    $ 99.00
  • Taslon Large Bill UV Cap with Neck Cape - Juniper UV Wear Cap MegaCI
    Taslon Large Bill UV Cap with Neck Cape - Juniper UV Wear Cap MegaCI J7250-WHT White

    Taslon Large Bill UV Cap with Neck Cape - Juniper UV Wear

    $ 29.75

    Embrace sun protection without compromise. This expansive UV cap features a commanding 180-degree brim with a 4.25" peak, paired with an innovative...

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    $ 29.75
  • Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats Bucket Hat Dorfman Hat Co.
    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats Bucket Hat Dorfman Hat Co. MC2-KAKI1 Khaki Small (55 cm)

    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats

    $ 26.99

    Trailer DPC Outdoor hats for hiking. Supplex® nylon boonie with vented mesh crown. Covered underbrim, 3" wide stitched brim. Wide elastic CoolMax® ...

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    $ 26.99
  • Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats

    Jr. Explorer by Wallaroo Hats

    $ 33.00

    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
  • 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

    Unisex Boonie with Contrast Under Brim - St. Johns Bay

    $ 17.00

    Embrace adventure with this ultralight Taslon boonie hat, engineered for explorers. The contrast under-brim and trim add distinctive style, while m...

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    $ 17.00
  • Stetson Hats Mesh Outback Hat for Men up to XXL - Mushroom Safari Hat Stetson Hats
    Stetson Hats Mesh Outback Hat for Men up to XXL - Mushroom Safari Hat Stetson Hats STC205MSHRM1 Mushroom Small

    Stetson Hats Mesh Outback Hat for Men up to XXL - Mushroom

    $ 51.99

    Embrace the spirit of adventure with this iconic Stetson mesh safari hat, engineered for the modern explorer. The breathable nylon mesh constructio...

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

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

    $ 51.99

    Embrace the great outdoors with confidence in this versatile Stetson mesh Outback hat. Built from durable nylon mesh, it's engineered to handle wha...

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    $ 51.99
  • 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)

    Pro Golf Flexfit Solid Baseball Cap - Scala Hats for Men

    $ 14.00

    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

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.