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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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  • Retail (33)

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  Made in the USA   A stiff blocked pork pie hat from Bailey, the Walsh Polished Wide Brim Wool Felt Pork Pie Hat is a sharp addition to their already stellar line of headwear. This is a contemporary take on a classic pork pie with a wider brim and a flatter, telescope crown that…

$187.00
Available Colors:
  • TAUPE
  • BLACK

  Made in the USA   Featuring Bailey's proprietary Elite Finish, the Winters Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an…

(3)
$164.05

  Made in Mexico   Crafted of woven and sewn palm leaf, the Palm Leaf Straw Lifeguard Hat by Jeanne Simmons is a great unisex style made for extended wear under the sun. Its classic lifeguard design features a cattleman crown, wide downturned brim, removable faux leather hat band and…

(13)
$37.76
Available Colors:
  • DARKNATURAL

  Made in the USA   Featuring Bailey's proprietary Elite Finish, the Bogan Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an unbelievably…

(1)
$164.05

  UPF 50+ Sun Protection   Prepare for sunny spring and summer days with the Wide Brim Toyo Straw Gambler Hat by Jeanne Simmons! Boasting the highest UPF sun protection rating possible (UPF 50+) with an extra wide brim, the Wide Brim Gambler has you (literally) covered from damaging…

(2)
$36.00
Available Colors:
  • NATURAL

  Bailey's new Duch Linen Plaid Five Panel Ivy Cap is crafted of breezy linen in a contemporary five-panel design. Featuring a cheery plaid pattern, the Duch is simply accented with a Bailey micro side pin and single snap bill. Great for a day on the green, or any other warm-weather outing,…

$72.25

  Made in the USA The Stedman Elite Velour Wool Felt Fedora Hat from Bailey is practical, sharp and classic. With a traditional fedora silhouette thanks to the center dent crown and wide brim, the Stedman is made of 100% wool with a velour finish to keep you warm during the winter…

$174.25

  Made in the USA The Bailey Wynn LiteFelt Wool Fedora Hat is a simple yet elegant hat.  This hat has been factory treated and is water and stain resistant.   Approx. 3 7/8" Teardrop crown 1 1/2" Pre-Snap Brim (Front) 1" Curled Brim (Sides & Back)   Made of:…

(2)
$110.50
Available Colors:

  Handwoven in Ecuador, Blocked & Finished in the USA   The Crispin Panama Straw Fedora Hat shows the craftmanship and care that goes into each design by Bailey! Adorned with only a braided leather hat band, the Crispin is anything but simple. The alternating weave in this…

$204.00
Available Colors:
  • NATURAL
  • NAVYBLUE

  Made in the USA   Featuring an elite finish, the 100% wool felt Ammon Wool Felt Teardrop Fedora Hat by Bailey is astonishingly silky to the touch. A classic teardrop crown (aka C-Crown) and all around downturned brim characterize this elegant fedora hat. Finished with a Japanese…

(1)
$164.05

  Made in the USA   May we present Bailey's Sterne Wool Felt Fedora Hat! This 3" stiff flat brim features a Japanese grosgrain ribbon hat band, braided cord overlay which has been secured in a fashionable knot. The raw edge brim is sharp and modern while the leather sweatband and…

$127.50
Available Colors:
  • KHAKI

  Made in the USA   Bailey 1922 debuts a new wool felt finish with the Croft Wool Felt Fedora Hat. Their 'beaver finish' creates a fuzzy and woolly texture. It has an 'outdoorsman' crown, a center pinch block with a wider center dent. The wide brim heightens the contemporary style,…

$170.00
Available Colors:
  • BLACK
  • TAUPE

  UPF 50+ Sun Protection   The Tweed/Check Rollable Visor by Jeanne Simmons offers the best in sun protection with a UPF 50+ rating while remaining conveniently packable and stylish. Made of toyo and polyester blend braiding in a great tweed and check design, this visor is not only…

$23.36
Available Colors:
  • BLACK
  • BROWN
  • TAUPE

  Just in time for spring, the Kids' Cherry Blossom Toyo Straw Sun Hat is a sweet new style from Jeanne Simmons. Featuring a classic sun hat design, this hat is detailed with bright red cherry blossoms embroidered along its brim. Flexible and packable, the Kid's Cherry Blossom Sun Hat is easy…

$18.00
Available Colors:
  • TAN

  UPF 50+ Sun Protection   Jeanne Simmons has created a new twist on an old favorite with the Tweed Toyo Straw Blend Floppy Sun Hat!   The braided toyo straw body has been infused with toyo straw and polyester for a tweed look in a straw hat! The braided and sewn materials…

(18)
$32.40
Available Colors:
  • WHITE
  • BLACK
  • TAN

  If you are an avid traveller and need a hat to match then the Packable Wheat Straw Sun Hat from Jeanne Simmons will be your companion. The 4-1/2" high cotton herringbone ribbon crown collapses when not worn, so it's perfect to pack flat in a suitcase. Braided wheat straw makes up the top of…

$22.46
Available Colors:
  • BLACK
  • NATURAL

  Made in the USA The Perry Lanolux Wool Felt Fedora Hat is crafted of 100% virgin wool with a luxurious sueded finish. Lanolux hats undergo an extra sanding process to create a lightweight and packable "Touch Me" finish for an unbelievably soft feel. Trimmed with a smooth leather…

(1)
$136.00

  Please Note: This style runs slightly large. We suggest you order one size smaller from your normal hat size.   Made in the USA   The Burnell LifeFelt Wool Fedora Hat by Bailey features a classic fedora silhouette with Bailey's top-rate LiteFelt® finish making the…

$94.50
Available Colors:
  • NATURAL

  Handwoven in Ecuador, Blocked & Finished in the USA   A beautiful traditional panama with some quality details, the Coram Panama Straw Fedora Hat by Bailey! The bubble crown and flat brim make this a classic, while the ventilation on the crown and a double layered, twisted…

$204.00
Available Colors:
  • NATURAL
  • TAWNY

  UPF 50+ Sun Protection   Looking for a wide brimmed hat that looks great and provides UV protection? Jeanne Simmons' Vineyard Toyo Straw Sun Hat is the hat for you! Featuring a wide brimmed design combined with the best UPF 50+ rating, the Vineyard isn't just for looks - it's…

(2)
$36.00
Available Colors:
  • TOASTTAN

  Made in the USA   The Colby Elite Superfine Velour Wool Felt Fedora Hat by Bailey in their newest finish, the Wool Velour. Meant to mimic fur felt, this ultimate finish has a sustainable purpose. The narrow pebbled leather hat band with a thick topstitch throughout gives rugged…

$195.50
Available Colors:
  • KHAKI

  The Jeanne Simmons Child's Classic Fedora Hat is a must have for your little one - a versatile straw fedora hat accompanied with a classic grosgrain ribbon hatband. Perfect for both boys and girls, the Child's Classic Fedora Hat has a sleek and clean look that easily compliments most…

$21.60
Available Colors:
  • TAN

  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

  UPF 50+ Sun Protection   Wistful and nostalgic, the Jeanne Simmons Overlap Brim and Bow Toyo Straw Sun Hat spotlights a captivating overlap brim, highlighted by its contrasting edge and matching slanted bow. Featuring a large 4-inch downturned brim and a maximum UPF rating of 50+,…

$28.76

  You'll always look stunning with the Louisa Milan Straw Boater Hat from Jeanne Simmons on your head. This great boater's most noteworthy feature is the large grosgrain ribbon hat band wrapping around the crown, sure to be eye-catching. This is so much more than just a simple straw hat! …

$50.40
Available Colors:
  • NATURAL

  A headwear piece that brings to mind abstract sculptures, there is no doubt that the Isabelle Sinamay Straw Fascinator Hat by Jeanne Simmons is a work of art. Constructed and shaped of sinamay straw, the disk base is asymmetrical and swirled which adds height and dimension. The sinamay straw…

$40.46
Available Colors:
  • BLACK
  • FUCHSIA
  • NATURAL

  Bailey's Piston Wool Felt Aussie Hat is a staple for any hat aficionado's closet. A classic wide-brim aussie hat silhouette with a teardrop crown, this hat is completely crushable/packable. The Piston is designed with a vegan leather bolo cord with metal tips. Fully lined in cotton, this hat…

$68.00
Available Colors:
  • TAN

  Made in the USA   The Imlay Knotted Shantung Straw Fedora Hat by Bailey has been created with a unique weave that adds texture to the body of this classic fedora. This style is simply decorated with partial suede hat band and Bailey's signature dipped nail. A finely woven sweatband…

$108.00
Available Colors:
  • NATURAL

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