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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
  • DPC Distressed Twill Cap with Frayed USA Flag for Small Heads Cap Dorfman Hat Co. C935-KAKI Khaki
    DPC Distressed Twill Cap with Frayed USA Flag for Small Heads Cap Dorfman Hat Co. C935-PUTTY Putty
    $ 15.00
    Dorfman Hat Co.

    DPC Distressed Twill Cap with Frayed USA Flag for Small Heads

    Garment washed twill unstructured baseball cap for small head sizes. Six panel cap with button top. Pre-curved bill, 2.5" wide with red, white, and...

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    $ 15.00
  • 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
  • Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Palm Beach by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 65.00
    Wallaroo Hats

    Petite Palm Beach by Wallaroo Hat Company

    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
  • Huntington Denim Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK459 Blue Small (54 cm)
    $ 28.00
    Sun N Sand Hats

    Huntington Denim Fedora for Small Heads - Sunny Dayz™ Hats

    Huntington stripe denim fedora hat for small head sizes. Inline braided raffia band. Dented crown with pinched front. Small brim with raffia edge, ...

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    $ 28.00
  • Small Size Fedora Hat with Palm Print Cotton Band - Sunny Dayz™ Safari Hat Sun N Sand Hats
    Small Size Fedora Hat with Palm Print Cotton Band - Sunny Dayz™ Safari Hat Sun N Sand Hats HK470 Natural Small (54 cm)
    $ 28.00
    Sun N Sand Hats

    Small Size Fedora Hat with Palm Print Cotton Band - Sunny Dayz™

    Classic summer hat for small heads. Dented and pinched crown. Brim is 2.5" wide. UPF 50+ rated UV blocking sun protection hat.  Ribbon inner band w...

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    $ 28.00
  • Cash Palm Printed Toyo Fedora for Small Heads - Sunny Dayz™ Safari Hat Sun N Sand Hats HK457 Brown Small (53.5 cm)
    $ 24.00
    Sun N Sand Hats

    Cash Palm Printed Toyo Fedora for Small Heads - Sunny Dayz™

    Unique printed palm leaves fedora hat. Tan hat with brown print. Classic dented and pinched crown. The brim is 2.5" wide. UPF 50+ rated UV-blocking...

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    $ 24.00
  • 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
    $ 7.50
    MegaCI

    Pro Style Twill Cap for Small Heads - MCI Hats

    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)
    $ 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
  • Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK455 Natural / Pink Small (54 cm)
    Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats Fedora Hat Sun N Sand Hats HK454 Tan / Blue Small (54 cm)
    $ 28.75
    Sun N Sand Hats

    Petite Tribal Band Fedora for Small Heads - Sunny Dayz™ Hats

    Tribal band fedora hat for small heads. Braid dented crown with pinched front. Tribal pattern woven band with raffia loop. Milan braid brim, 2" wid...

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    $ 28.75
  • 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
  • Slicker Wool Felt Teardrop Fedora Hat - Biltmore Hats Fedora Hat Biltmore Hats BF1240SLIK30SM Fawn Small  (55 cm)
    Sale
    Original Price $ 143.00
    Current Price $ 98.75
    Biltmore Hats

    Slicker Wool Felt Teardrop Fedora Hat - Biltmore Hats

    Handcrafted wool felt fedora hat made in the USA. Teardrop crown with deep front pinch.  Curled up brim, 3" wide. Grosgrain ribbon band with wingti...

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    Original Price $ 143.00
    Current Price $ 98.75
    Sale
  • 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
  • Junior Reversible Wide Brim Cotton Boonie Hat - Karen Keith Hats Bucket Hat Great hats by Karen Keith CH98K-J Pink S/M (56-57 cm)
    Junior Reversible Wide Brim Cotton Boonie Hat - Karen Keith Hats Bucket Hat Great hats by Karen Keith CH98K-F Black S/M (56-57 cm)
    $ 18.00
    Great hats by Karen Keith

    Junior Reversible Wide Brim Cotton Boonie Hat - Karen Keith Hats

    Wide brim cotton bucket hat. Square, flat crown top. Stitched flat brim, 2.5" wide. Tropical print on one side, solid color on the other side. UPF ...

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    $ 18.00
  • 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
  • Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons
    Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons JS8439BZ Bronze Small (56 cm)
    $ 24.00
    Jeanne Simmons

    Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats

    Discover timeless summer style with this petite straw fedora, expertly crafted for smaller head sizes. The soft paper braid construction offers bre...

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    $ 24.00
  • 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
  • Classic Woven Straw Summer Fedora Hat for Small Heads - JSA Hats Fedora Hat Jeanne Simmons JS1237TAN Tan Small (56cm)
    Classic Woven Straw Summer Fedora Hat for Small Heads - JSA Hats Fedora Hat Jeanne Simmons JS1237NAT Natural Small (56cm)
    $ 24.00
    Jeanne Simmons

    Classic Woven Straw Summer Fedora Hat for Small Heads - JSA Hats

    Timeless fedora silhouette featuring a refined teardrop crown with subtle front pinch detail. The narrow 2-inch brim offers understated elegance, w...

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    $ 24.00
  • 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
  • Orange and Navy Band Straw Fedora for Small Heads - Sunny Dayz™ Fedora Hat Sun N Sand Hats
    Orange and Navy Band Straw Fedora for Small Heads - Sunny Dayz™ Fedora Hat Sun N Sand Hats HKYOS197A Natural Small (54 cm)
    $ 16.00
    Sun N Sand Hats

    Orange and Navy Band Straw Fedora for Small Heads - Sunny Dayz™

    Straw braid fedora hat for petite head sizes. Inline orange and navy stripe band. Dented crown with pinched front. Small brim, 1.75" wide. UPF 50+ ...

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    $ 16.00
  • 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

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.