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Men's Hats for Small Heads

  • Vintage Bronco Full-Grain Leather Outback Hat - Red Rock Hats Safari Hat Red Rock Hats 1081HI3S Hickory Small (53 cm)
    $ 95.00
    Red Rock Hats

    Vintage Bronco Full-Grain Leather Outback Hat - Red Rock Hats

    Red Rock Fold-A-Bull Australian Leather Hat Crafted from premium full-grain Australian cattle leather, the Fold-A-Bull is built for adventure. Its ...

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    $ 95.00
  • Premium Cattle Suede Mesh Crown Cooler Hat - Red Rock Hats Safari Hat Red Rock Hats 1074BR5L Brown Large (57 cm)
    Premium Cattle Suede Mesh Crown Cooler Hat - Red Rock Hats Safari Hat Red Rock Hats 1074OC5L Dark Brown Large (57 cm)
    $ 85.00
    Red Rock Hats

    Premium Cattle Suede Mesh Crown Cooler Hat - Red Rock Hats

    Red Rock Suede Cooler Hat – Lightweight, Packable, and Made for the Outback Blending classic Australian outback style with travel-ready features, t...

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    $ 85.00
  • Bushie Genuine Cattle Leather Mesh Crown Cooler Hat - Red Rock Hats Safari Hat Red Rock Hats
    Bushie Genuine Cattle Leather Mesh Crown Cooler Hat - Red Rock Hats Safari Hat Red Rock Hats 1032TC4M Tan Suede Medium (56 cm)
    $ 85.00
    Red Rock Hats

    Bushie Genuine Cattle Leather Mesh Crown Cooler Hat - Red Rock Hats

    Red Rock Leather Cooler Hat – Packable, Breathable, Adventure-Ready Stay cool and protected wherever your travels take you with the Red Rock Leathe...

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    $ 85.00
  • Woven Straw Cowboy Hat with Turquoise Concho - Kenny Keith Hats Cowboy Hat Great hats by Karen Keith TM10L-Ax Natural Small (56 cm)
    $ 52.00
    Great hats by Karen Keith

    Woven Straw Cowboy Hat with Turquoise Concho - Kenny Keith Hats

    Knobby woven fine Bangkok toyo straw hat. The darker crown top and brim edge create a worn look. Vented teardrop crown, approximately 4" tall. Curl...

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    $ 52.00
  • Justin Hats - Travis Fine Palm Wide Brim Hat Safari Hat Justin Hats JS19TBTRAV4054 Natural 6 3/4 (54 cm)
    $ 59.00
    Justin Hats

    Justin Hats - Travis Fine Palm Wide Brim Hat

    Discover the Travis Fine Palm—a hand-crafted Mexican palm hat that brings effortless style to any adventure. This safari-inspired beauty features a...

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    $ 59.00
  • 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)
    $ 99.00
    Tilley Endurables Hats

    The Airflo® Tilley Hat - Medium Brim LTM5 Boonie

    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)
    $ 99.00
    Tilley Endurables Hats

    The Airflo® Tilley Hat - Broad Brim LTM6 Boonie

    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)
    $ 99.00
    Tilley Endurables Hats

    Modern Airflo® Boonie Hat - Tilley Hats

    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
  • Sierra Burnt Palm Leaf Western Hat - Tula Hats Cowboy Hat Tula Hats
    Sierra Burnt Palm Leaf Western Hat - Tula Hats Cowboy Hat Tula Hats TU1-8000 Burnt Palm Small (55 cm)
    $ 48.00
    Tula Hats

    Sierra Burnt Palm Leaf Western Hat - Tula Hats

    The Sierra Burnt Palm Leaf Western Hat combines timeless cowboy aesthetics with practical sun protection. Expertly handcrafted from 100% palm fiber...

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    $ 48.00
  • Senna Handwoven Shantung Flat Brim Hat - Biltmore USA Safari Hat Biltmore Hats BS344SENA34MD Natural Medium  (57 cm)
    Senna Handwoven Shantung Flat Brim Hat - Biltmore USA Safari Hat Biltmore Hats BS344SENA34SM Natural Small  (55 cm)
    $ 95.00
    Biltmore Hats

    Senna Handwoven Shantung Flat Brim Hat - Biltmore USA

    Handwoven shantung wide brim fedora hat made in the USA. Classic center dent and pinch front crown. Flat brim, 3.5" wide. Wide grosgrain ribbon ban...

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    $ 95.00
  • Caliber Palm Teardrop Curled Brim Sun Hat - Biltmore Hats Safari Hat Biltmore Hats BS70N1CALI3601SM Natural Small  (55 cm)
    Caliber Palm Teardrop Curled Brim Sun Hat - Biltmore Hats Safari Hat Biltmore Hats
    $ 89.00
    Biltmore Hats

    Caliber Palm Teardrop Curled Brim Sun Hat - Biltmore Hats

    Hand woven authentic Mexican palm sun hat. Classic teardrop crown hat with pinched front. Curled brim, approximately 3.25" wide. Guatemalan woven b...

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    $ 89.00
  • 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
    $ 29.75
    MegaCI

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

    Extra wide bill UV cap with extended back flap. Five panel crown with mesh insert for ventilation. Wide dimensional 180 degree brim, 4.25" peak. Ex...

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    $ 29.75
  • Mini Ripstop Performance Sun Visor - Juniper UV Wear Visor Cap MegaCI
    Mini Ripstop Performance Sun Visor - Juniper UV Wear Visor Cap MegaCI J7256nv Navy
    $ 15.00
    MegaCI

    Mini Ripstop Performance Sun Visor - Juniper UV Wear

    Mini ripstop performance sport visor. New 3D grid textured mesh inner band enhances ventilation and keep you cool. Comfortable cushioned moisture w...

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    $ 15.00
  • Washed Cotton Twill Pro Style Visor - Mega Cap Visor Cap MegaCI
    Washed Cotton Twill Pro Style Visor - Mega Cap Visor Cap MegaCI MC4056kh Khaki
    $ 10.00
    MegaCI

    Washed Cotton Twill Pro Style Visor - Mega Cap

    Washed cotton twill sport visor. Three panel band with pro stitch. Curved bill, 2.75" wide, with pro-stitching detail. Self-fabric sweatband and ho...

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    $ 10.00
  • Men's Cotton Twill Pro Style Visor - Mega Cap Visor Cap MegaCI MC4121Ast Stone
    $ 10.00
    MegaCI

    Men's Cotton Twill Pro Style Visor - Mega Cap

    Washed cotton twill sport visor. Comfortable cushioned band all-day comfort sun protection visor. Three panel band with pro stitch. Curved bill, 2....

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    $ 10.00
  • Pistol Mexican Palm Flat Brim Hat - Biltmore Hats Safari Hat Biltmore Hats BS70TFPISLXLS Natural Small  (55 cm)
    $ 89.00
    Biltmore Hats

    Pistol Mexican Palm Flat Brim Hat - Biltmore Hats

    Handwoven authentic Mexican palm outback style hat. Classic teardrop crown hat with pinched front. Solid rust color grosgrain ribbon band. Biltmore...

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    $ 89.00
  • Water Repellent Poplin Bucket Hat, British Tan - DPC Hats Bucket Hat Dorfman Hat Co.
    Water Repellent Poplin Bucket Hat, British Tan - DPC Hats Bucket Hat Dorfman Hat Co. 830D-DTAN1 Tan Small (55 cm)
    $ 22.50
    Dorfman Hat Co.

    Water Repellent Poplin Bucket Hat, British Tan - DPC Hats

    This water-repellent bucket hat from Dorfman Pacific Company is your new rainy-day companion. Built with a flat crown and subtly tapered sides for ...

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    $ 22.50
  • Garment Washed Cotton Boonie Hat with Chin Strap - MCI Bucket Hat MegaCI MC7804A-BGs Beige Small (55 cm)
    Garment Washed Cotton Boonie Hat with Chin Strap - MCI Bucket Hat MegaCI MC7804A-OLs Olive Small (55 cm)
    $ 19.50
    MegaCI

    Garment Washed Cotton Boonie Hat with Chin Strap - MCI

    Classic pigment dyed twill boonie hat for fishing and hiking. Solid fabric crown provides excellent sun protection. Stitched bound brim 2.75" wide....

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    $ 19.50
  • Natural Palm Leaf Wide Brim Safari Hat - SetarTrading Hats Safari Hat SetarTrading Hats 7338x Natural Palm Small (55 cm)
    Natural Palm Leaf Wide Brim Safari Hat - SetarTrading Hats Safari Hat SetarTrading Hats
    $ 32.00
    SetarTrading Hats

    Natural Palm Leaf Wide Brim Safari Hat - SetarTrading Hats

    Natural tripilla palm straw sun hat for men and women. Tight micro-braided strands create high quality sun protection hats. Shallow crow, 3.75" wit...

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    $ 32.00
  • Straw Lifeguard Hat with Blue Hibiscus Print Underbrim - Kenny K. Hats Lifeguard Hat Great hats by Karen Keith LM9-Cl Natural Large (59 cm)
    Straw Lifeguard Hat with Blue Hibiscus Print Underbrim - Kenny K. Hats Lifeguard Hat Great hats by Karen Keith LM9-Cs Natural Small (55 cm)
    $ 29.00
    Great hats by Karen Keith

    Straw Lifeguard Hat with Blue Hibiscus Print Underbrim - Kenny K. Hats

    Natural rush straw straw lifeguard hat. Wide brim, 4.5", with blue Hawaii hibiscus print cotton underbrim and bounding. Rope tie and chin strap. Ke...

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    $ 29.00
  • 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

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.