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    • Small
      Pequeuño
      Size
      6
      3/4
      -
      6
      7/8
      Tamaño
      21
      1/8
      "
      -
      21
      1/2
      "
      54
      cm
      -
      55
      cm
    • Medium
      Medio
      Size
      7
      -
      7
      1/8
      Tamaño
      21
      7/8
      "
      -
      22
      1/4
      "
      56
      cm
      -
      57
      cm
    • large
      Grande
      Size
      7
      1/4
      -
      7
      3/8
      Tamaño
      22
      5/8
      "
      -
      23
      "
      58
      cm
      -
      59
      cm
    • X-Large
      X-Grande
      Size
      7
      1/2
      -
      7
      5/8
      Tamaño
      23
      1/2
      "
      -
      23
      7/8
      "
      60
      cm
      -
      61
      cm
    • XX-Large
      XX-Grande
      Size
      7
      3/4
      -
      7
      7/8
      Tamaño
      24
      1/4
      "
      -
      24
      5/8
      "
      62
      cm
      -
      63
      cm
    • XXX-Large
      XXX-Grande
      Size
        8
       - 
      8 +
      Tamaño
      25
      "
      -
      25
      3/8
      "
      64
      cm
      -
      65
      cm
  • This is a General Hat Sizing Chart: Please read each hat product page for further sizing information.
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141 - 168 of 244 Products
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  A new staple for any flat cap fan, the Liam Linen Cotton Ivy Cap by Bailey! Made of a soft cotton and linen blend, this hat features a stripe pattern. Features a sewn bill, Bailey side pin, cotton twill sweatband and cloth lining.   Approx. 9 1/2" Front to Back, Flat 9 1/2" Side to…

$90.00

  Made in the USA Bailey's Winstone Raindura Straw Fedora Hat is the most shape retentive, durable straw hat on the market thanks to the exclusive Raindura® finish. This revolutionary process involves thermosetting yarn which has been handwoven inside a straw body. It is then…

$135.00
Available Colors:
  • NATURAL

  Handwoven in Ecuador; Blocked & Finished in the USA   Introducing the Rene Two-Tone Panama Straw Fedora Hat by Bailey featuring a striking two-tone contrast weave. The Rene is artisanally handwoven in Ecuador then blocked and finished in the USA by expert Bailey craftsmen. The…

$250.00
Available Colors:
  • BROWNBLACK
  • NATURALSILVER

  Calling all travelers, adventure-seekers, jetsetters, we have just the hat for your on-the-go needs, Bailey's Balans Roll Up Toyo Straw Fedora Hat. Made from a toyo straw that has been crafted into an ultra-soft lightweight braid which can be rolled and packed to easily fit into a bag or…

$100.00

  Featuring a masculine distressed finish, the Lazar Suede Leather Ivy Cap is a deluxe flat cap by Bailey 1922. Crafted of genuine pig skin leather with a distressed suede finish, the Lazar is a distinctive cap for flat cap lovers. Four small panels comprise the back half of the cap while the…

(2)
$102.00
Available Colors:
  • COFFEE

  Bailey's Leif Linen Cotton Pub Cap is a buttery soft flat cap for warm weather thanks to the blend of linen and cotton. With a contour 8-panel shape, the Leif is designed to fit snugly. The stripe pattern completes this overall classic style.    Approx. 9 1/2" Front to Back - Flat…

$90.00
Available Colors:
  • CREAM
  • NAVYBLUE

  Handwoven in Ecuador; Finished in the USA   The Hernen Two-Tone Panama Straw Fedora Hat by Bailey has a unique two-tone weave throughout the hat, giving it a sophisticated and modern look. Woven by hand in Ecuador by skilled artisans then blocked and finished in the USA by expert…

$225.00

  Made in the USA   Make a statement with the Caprole Wool LiteFelt Walker Trilby Hat by Bailey 1922! The Caprole is a unique trilby that is water resistant, stain repellent, and shape retentive making it ideal for styling anywhere you go. It includes a removable side duck feather, a…

$123.25

  Handwoven in Ecuador; Blocked & Finished in the USA   Bailey's Moren Vented Panama Straw Western Hat is a genuine Panama straw hat handwoven in Ecuador then blocked and finished in the USA. Featuring geometric venting along its classic cattleman crown, the Moren is finished…

$250.00

  Made in the USA   A classic styled fedora by Bailey, the Ernest Elite Velour Wool Felt Fedora Hat. With a wide Japanese grosgrain ribbon hat band which has been finished with a single horizontal pleated tail. A dipped nail is strategically tucked behind, its a Bailey signature. And…

$135.00
Available Colors:
  • BROWN
  • BLEACH

  Made in the USA The Switchback is a classic Wind River® by Bailey western style. Made in the USA of their exclusive wool LiteFelt® that is both packable/crushable and water repellent, the Switchback features a braided leather hat band and curved brim for a timeless Aussie/western…

(5)
$135.00
Available Colors:
  • BLACK
  • PECAN

  Made in the USA   Bailey's Architect Fur Felt Cattleman Western Hat is the luxury experience in headwear. Crafted of superior fur felt, that you can keep in pristine condition thanks to the included hat brush. Handcrafted, this style takes a traditionally western silhouette with…

$382.50
Available Colors:
  • BLACK

  Handwoven in Ecuador, Blocked & Finished in the USA   With the Racer Panama Straw Fedora Hat by Bailey you get both comfort and style. This is a custom panama handcrafted in Ecuador with a woven crochet teardrop crown and brisa snap brim. Finishing touches are the Japanese…

$225.00
Available Colors:
  • NATURAL

  Made in Mexico   Bailey presents the Koslo II 15X Shantung Straw Western Hat just in time for warm weather! The Koslo features premium 15X shantung straw with a firm finish in a stylish two-tone weave. Its timeless cattleman crown features vent detailing and is finished with a…

$160.00

  Made in the USA   The Godwin Elite Superine Velour Wool Felt Fedora features Bailey's newest finish, a wool velour. Designed with sustainability in mind, this finish is made to mimic the feel of fur felt but is made completely of wool. A buttery-soft genuine leather hat band with a…

$212.50
Available Colors:
  • EGGPLANT
  • TAUPE

  Made in the USA Introducing the Firehole Crushable Wool LiteFelt Western Hat by Bailey. Crafted with Bailey's exclusive LiteFelt® finish, the Firehole Western is not only incredibly soft and packable/crushable but also water repellent. Able to retain its shape, the Firehole is up…

$135.00
Available Colors:
  • FAWN

  Made in Mexico   Bailey presents the Rausch 7X Jute Straw Western Hat just in time for summer! Featuring an airy jute straw weave, the Rausch is lightweight and incredibly breathable. Details include a shallow cattleman crown (center dent, pinched sides), vented detailing along the…

$90.00
Available Colors:
  • NATURAL

  Made in the USA   The McCrae Wool Felt Gus Western Hat from Bailey features one of the most unique and oldest crown shapes in western headwear, the Gus crown. This crown was made famous by Robert Duvall's character in Lonesome Dove, Augustus McCrae, abbreviated to Gus. Made in the…

$160.00
Available Colors:
  • BLACK

  Made in the USA   Get ready for something new with the Melton LiteStraw® Seagrass Gambler Hat from Bailey! This unique hat is made with seagrass, a durable and stain-resilient material perfect for any stylish adventurer. No matter your plans, this hat should be your go-to! …

(4)
$160.00
Available Colors:
  • NATURAL

  Made in the USA   Introducing Bailey 1922’s Appley Elite Velour Wool Felt Fedora Hat, a true epitome of sophistication and American craftsmanship. Made with 100% wool felt, this hat showcases both luxury and warmth, making it a perfect addition to your fall or winter wardrobe.…

$165.75

  Handwoven in Ecuador; Blocked & Finished in the USA   The Keats Vented Panama Straw Fedora Hat combines artisanal handwoven Panama straw and the best of Bailey American craftsmanship in one stunning hat style. Starting with its handwoven body in striking colors, the Keats is…

$240.00

  Made in the USA   Introducing the Oswego Endura Raindura Straw Outback Hat, part of the Bailey Wind River® collection of rugged outdoor styles. The Oswego is crafted in the USA using Bailey's exclusive Raindura finish that makes the straw both water resistant and shape retentive.…

$138.00
Available Colors:
  • NATURAL

  Made in New Zealand   You want to be dry and protected when the weather takes a turn for the worst so make sure to always have your packable Hills Hats of New Zealand Hydrotex Rain Bucket Hat with you. The unique characteristics of the Hydrotex Bucket has been tested to resist both…

(2)
$48.00
Available Colors:
  • BLACK

  Made in the USA   Dress to impress with the Pageant II 2X Wool Felt Western Hat by Bailey! Featuring a classic cattleman crown and dramatic flared brim, the Pageant II is crafted of genuine 2X wool felt. Trimmings are kept at a minimum for an elegant finish and include a self-felt…

$150.00
Available Colors:
  • WHITE

  Made in Mexico   Bailey's Derren Bangora Straw Western Hat features a bangora straw build with a firm finish and handsome detailing. Its classic cattleman crown is accented with stylized weaving along its sides and trimmed with a narrow grosgrain hat band and Bailey side pin. Its…

$85.00
Available Colors:
  • IVORY
  • TAN

  The Lou Herringbone Plaid Wool Ivy Cap is a new wool blend cap from Bailey! With a multicolored herringbone plaid pattern, it is fully lined and boasts a comfortable sweatband. It's an attractive yet neutral look that is perfect all year round.   Approx. 10" Front to Back, Flat 10"…

$68.00

  Dress up like your favorite loveable feline in the Cat in the Hat Deluxe Headband. A mini version of the signature striped hat sits atop a soft cat ear headband.   Approx. 3 1/2" Tall Mini Top Hat   Made of: 100% Polyester   Size: One Size Fits Most  

$16.95
Available Colors:
  • MULTI

  Handwoven in Ecuador; Finished in the USA   Bailey's Ezra Vented Panama Straw Fedora Hat is a unique piece beautifully crafted with a ventilation pattern in the hat's crown. Trimmed with a distressed leather laced hat band and a removable side feather, this hat is handcrafted from…

$240.00
Available Colors:
  • NATURAL

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