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Men's Hats for Small Heads

  • Straw Lifeguard Hat with Surfboard Print Underbrim - Kenny K. Hats Lifeguard Hat Great hats by Karen Keith LM9-Dl Natural Large (59 cm)
    Straw Lifeguard Hat with Surfboard Print Underbrim - Kenny K. Hats Lifeguard Hat Great hats by Karen Keith LM9-Ds Natural Small (55 cm)
    $ 29.00
    Great hats by Karen Keith

    Straw Lifeguard Hat with Surfboard Print Underbrim - Kenny K. Hats

    Natural rush straw straw lifeguard hat. Wide brim, 4.5", with surfboard print cotton underbrim and bounding. Rope tie and chin strap. UPF 50+ sun h...

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    $ 29.00
  • Distressed Woven Straw Cowboy Hat, XS to XL Sizes - Karen Keith Hats Cowboy Hat Great hats by Karen Keith RC12D-XS Natural Extra-Small (20 7/8")
    $ 45.00
    Great hats by Karen Keith

    Distressed Woven Straw Cowboy Hat, XS to XL Sizes - Karen Keith Hats

    Summer straw cowboy hat with darker, worn look crown tip and brim edge. Criss cross woven straw. Over-welt brim, 3.25" wide. Double rope chin tie w...

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    $ 45.00
  • Supplex® Nylon Boonie with Covered Underbrim - DPC Global Hats Bucket Hat Dorfman Hat Co.
    Supplex® Nylon Boonie with Covered Underbrim - DPC Global Hats Bucket Hat Dorfman Hat Co. MC1-KAKI1 Khaki Small (55 cm)
    $ 24.00
    Dorfman Hat Co.

    Supplex® Nylon Boonie with Covered Underbrim - DPC Global Hats

    Evergreen DPC Outdoor hats for fishing. Supplex® nylon boonie hat. Covered underbrim reduces glare. Stitched brim, 3.25" wide. Wide elastic CoolMax...

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    $ 24.00
  • 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)
    $ 26.99
    Dorfman Hat Co.

    Supplex® Nylon Boonie with Mesh Crown - DPC Global Hats

    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
  • Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats
    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats TU-15000S Burnt Palm Small (56-57 cm)
    $ 45.00
    Tula Hats

    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats

    Discover refined sun protection with this distinguished outback gambler hat, expertly crafted for smaller head sizes. Featuring a striking burnt pa...

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    $ 45.00
  • Garment Washed Twill Mesh Crown Safari Hat - Dorfman Hat Co. Safari Hat Dorfman Hat Co.
    Garment Washed Twill Mesh Crown Safari Hat - Dorfman Hat Co. Safari Hat Dorfman Hat Co. 863M-PUTTY1 Putty Small (55 cm)
    $ 31.99
    Dorfman Hat Co.

    Garment Washed Twill Mesh Crown Safari Hat - Dorfman Hat Co.

    Trailman breezy small brim summer safari hat.  Creased crown with mesh sidewall will provide good ventilation.  Downward sloping stitched and bound...

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    $ 31.99
  • Crushable Water Repellent Wool Felt Fedora Hat - Scala Hat Fedora Hat Scala Hats
    Crushable Water Repellent Wool Felt Fedora Hat - Scala Hat Fedora Hat Scala Hats DF109-BLK1 Black Small (55 cm)
    $ 70.00
    Scala Hats

    Crushable Water Repellent Wool Felt Fedora Hat - Scala Hat

    This timeless wool felt fedora combines sophisticated style with practical functionality. Crafted from 100% wool felt, it features a distinctive pi...

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    $ 70.00
  • Authentic Basque French Wool Beret - Heritage Par Laulhere Beanie Laulhere
    Authentic Basque French Wool Beret - Heritage Par Laulhere Beanie Laulhere 51-BLK1 Black Small (55 cm)
    Sale
    Original Price $ 89.00
    Current Price $ 47.65
    Laulhere

    Authentic Basque French Wool Beret - Heritage Par Laulhere

    This beautiful French military beret was made by the iconic Heritage par Laulhere company. Beret is approximately 10" diameter with top tassel, cab...

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    Original Price $ 89.00
    Current Price $ 47.65
    Sale
  • Tweed Patchwork Flat Cap - Dorfman Hats Flat Cap Dorfman Hat Co.
    Tweed Patchwork Flat Cap - Dorfman Hats Flat Cap Dorfman Hat Co. MW231-SM Brown Small/Medium
    $ 30.00
    Dorfman Hat Co.

    Tweed Patchwork Flat Cap - Dorfman Hats

    Crafted from a balanced wool and polyester blend, this distinguished flat cap showcases an elegant patchwork design in rich blue and brown tweed to...

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    $ 30.00
  • Solarweave® Mesh Crown Safari Hat, Camel - DPC Outdoor Design Safari Hat Dorfman Hat Co.
    Solarweave® Mesh Crown Safari Hat, Camel - DPC Outdoor Design Safari Hat Dorfman Hat Co. SPF4-CAML1 Camel Small (55 cm)
    $ 39.99
    Dorfman Hat Co.

    Solarweave® Mesh Crown Safari Hat, Camel - DPC Outdoor Design

    Lightweight, airy cotton safari hat. Mesh crown sidewall, cotton crown top provides breezy sun protection. Stitched, bound brim, 3" wide. Dark unde...

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    $ 39.99
  • Small Heads Wide Brim Summer Fedora Hat- Jeanne Simmons Hats Fedora Hat Jeanne Simmons JS6761tns Tan Small (56cm)
    $ 24.00
    Jeanne Simmons

    Small Heads Wide Brim Summer Fedora Hat- Jeanne Simmons Hats

    Perfect for petite frames, this charming fedora delivers classic style with a practical twist. The generous 2.5" brim shields your face while the p...

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    $ 24.00
  • Small Heads Straw Summer Fedora Hat - Milani Hats Fedora Hat Milani Hats KFD107bkx Black Jr. L/XL (54 cm)
    Small Heads Straw Summer Fedora Hat - Milani Hats Fedora Hat Milani Hats KFD107ntx Natural Jr. L/XL (54 cm)
    $ 15.00
    Milani Hats

    Small Heads Straw Summer Fedora Hat - Milani Hats

    Perfect for petite heads and warm-weather adventures, this charming straw fedora brings vintage flair to your summer style. Featuring a distinctive...

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    $ 15.00
  • Solarweave® Mesh Crown Safari Hat, Oatmeal - DPC Outdoor Design Safari Hat Dorfman Hat Co.
    Solarweave® Mesh Crown Safari Hat, Oatmeal - DPC Outdoor Design Safari Hat Dorfman Hat Co. SPF4-OAT1 Oatmeal Small (55 cm)
    $ 39.99
    Dorfman Hat Co.

    Solarweave® Mesh Crown Safari Hat, Oatmeal - DPC Outdoor Design

    Lightweight, airy cotton safari hat. Mesh crown sidewall, cotton crown top provides breezy sun protection. Stitched, bound brim, 3" wide. Dark unde...

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    $ 39.99
  • Small Heads Classic Cotton Bucket Hat - Boardwalk Style Hats Bucket Hat Boardwalk Style Hats
    Small Heads Classic Cotton Bucket Hat - Boardwalk Style Hats Bucket Hat Boardwalk Style Hats DACH06nv Navy-White Small (56 cm)
    $ 9.00
    Boardwalk Style Hats

    Small Heads Classic Cotton Bucket Hat - Boardwalk Style Hats

    Discover timeless style with this vintage-inspired bucket hat designed specifically for smaller head sizes. Featuring a shallow, flat-top crown and...

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    $ 9.00
  • Small Heads Pigment Dyed Garment Washed Twill Bucket Hat - DPC Bucket Hat Dorfman Hat Co. C835 Sand Jr. S/M (53-54 cm)
    Small Heads Pigment Dyed Garment Washed Twill Bucket Hat - DPC Bucket Hat Dorfman Hat Co. C835 Stone Jr. S/M (53-54 cm)
    $ 13.50
    Dorfman Hat Co.

    Small Heads Pigment Dyed Garment Washed Twill Bucket Hat - DPC

    Traditional cotton bucket hat for small head sizes. Pigment dyed garment washed twill. 2" wide stitched, bound brim. Two metal eyelets on both side...

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    $ 13.50
  • Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons
    Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons js1239-TAN Tan XS (55 cm)
    $ 24.00
    Jeanne Simmons

    Small Heads Straw Fedora Hat with Black Band - Jeanne Simmons Hats

    Meet your new favorite travel companion! This charming paper braid fedora is designed specifically for smaller heads and brings instant personality...

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    $ 24.00
  • Fine Braid Safari Hat with Black Band - Scala Hats for Men Safari Hat Scala Hats
    Fine Braid Safari Hat with Black Band - Scala Hats for Men Safari Hat Scala Hats ms449m Natural Small/Medium (56-57 cm)
    $ 28.50
    Scala Hats

    Fine Braid Safari Hat with Black Band - Scala Hats for Men

    This men's safari hat from Scala combines timeless design with practical performance features. Constructed from fine paper braid, it offers UPF 50+...

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    $ 28.50
  • Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Sedona by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Petite Sedona by Wallaroo Hat Company

    The Petite Sedona brings rustic charm and sun-smart performance to smaller head sizes. Its woven paper-braid texture offers breathable comfort, whi...

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    $ 61.00
  • Head'n Home Crusher Outback Leather Hat up to 3XL- Bomber Brown Safari Hat Head'N'Home Hats
    Head'n Home Crusher Outback Leather Hat up to 3XL- Bomber Brown Safari Hat Head'N'Home Hats crusherBBML Brown Small
    $ 157.00
    Head'N'Home Hats

    Head'n Home Crusher Outback Leather Hat up to 3XL- Bomber Brown

    Crafted right here in the USA, this rugged leather Outback hat is built for adventure seekers who refuse to compromise. The aged, antiqued leather ...

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    $ 157.00
  • Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    Jr. Explorer by Wallaroo Hats Bucket Hat Wallaroo Hats
    $ 33.00
    Wallaroo Hats

    Jr. Explorer by Wallaroo Hats

    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
  • Waxed Canvas Casual Safari Hat - Texas Gold Hats Safari Hat Texas Gold Hats
    Waxed Canvas Casual Safari Hat - Texas Gold Hats Safari Hat Texas Gold Hats jr7017 Ivory Small (56 cm)
    $ 19.00
    Texas Gold Hats

    Waxed Canvas Casual Safari Hat - Texas Gold Hats

    Stiff waxed canvas men's safari hat. Dented crown with side pinch. Vented mid-crown. Leather band with contrast color twisted overlay. Elastic comf...

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    $ 19.00
  • Raw Denim  LIL'BRIMS - Blue Cap Ultra Sport
    Raw Denim  LIL'BRIMS - Blue Cap Ultra Sport lbfa1820m Dark Denim Medium/Large
    Sale
    Original Price $ 33.00
    Current Price $ 5.00
    Ultra Sport

    Raw Denim LIL'BRIMS - Blue

    Six panel denim cap. Up turned curved small faux leather bill. 1.75" peak. Button top. Sewn eyelets on each panel. Lil'Brim pin accent. Cotton and ...

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    Original Price $ 33.00
    Current Price $ 5.00
    Sale
  • Quilted  LIL'BRIMS - Black Cap Ultra Sport
    Quilted  LIL'BRIMS - Black Cap Ultra Sport lbfa1834m Black Medium/Large
    Sale
    Original Price $ 33.00
    Current Price $ 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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    Original Price $ 33.00
    Current Price $ 5.00
    Sale
  • No Donut  LIL'BRIMS - Black Cap Ultra Sport
    No Donut  LIL'BRIMS - Black Cap Ultra Sport
    Sale
    Original Price $ 33.00
    Current Price $ 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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    Original Price $ 33.00
    Current Price $ 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
  • 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
    $ 17.00
    Dorfman Hat Co.

    Unisex Boonie with Contrast Under Brim - St. Johns Bay

    Feather weight Taslon fishing bucket hat. Contrast trim and under-brim. Metal eyelets. Toggle sizing band. 2.5" wide soft brim. UPF 50+ sun protect...

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    $ 17.00
  • Brushed Twill Mesh Crown Safari with Chin Cord - DPC Outdoor Design Safari Hat Dorfman Hat Co.
    Brushed Twill Mesh Crown Safari with Chin Cord - DPC Outdoor Design Safari Hat Dorfman Hat Co. 864M-KAKI1 Khaki Small (55 cm)
    $ 39.50
    Dorfman Hat Co.

    Brushed Twill Mesh Crown Safari with Chin Cord - DPC Outdoor Design

    Lightweight, airy safari hat provides excellent sun protection. Dented crown with mesh sidewall.  Slightly downward sloping brim, 3" wide. Chin cor...

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    $ 39.50
  • 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
    $ 51.99
    Stetson Hats

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

    Legendary Stetson® Hats for men. Grand Canyon breezy mesh safari hat.  Slightly curving brim, 2.75" wide with covered underbrim and crown top for m...

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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
    $ 51.99
    Stetson Hats

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

    Outback style breezy mesh hat. Nylon mesh construction makes this hat tough enough to take along for all your wet of dry outdoor adventures. Covere...

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    $ 51.99
  • Adventurer Low Profile Safari Hat - Henschel Hats Safari Hat Henschel Hats H5316-KHS Khaki Small (22")
    Adventurer Low Profile Safari Hat - Henschel Hats Safari Hat Henschel Hats H5316-EAS Earth Small (22")
    $ 47.00
    Henschel Hats

    Adventurer Low Profile Safari Hat - Henschel Hats

    Packable lightweight hat for all adventurers. Flat low rise cotton crown top, sloping toward back. Mesh side panels to maximize airflow. Cotton bri...

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    $ 47.00

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.