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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 (41)

Bailey Xxl

1 - 28 of 41 Products
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…is a great hat to spend the day walking around town in without feeling over heated.   Approx. 4" Center Pinch Crown 2" Snap Brim   Made of: 100% Polypropylene   Comfort Sweatband Unlined Bailey Side Pin   Sizes: S, M, L, XL, and XXL; fits true to size.  

(1)
$66.00

…Approx. 3 1/2" Teardrop Crown 1 5/8" Snap Brim   Made of: 100% Polypropylene Braid   Black Bailey Side Pin Striped Grosgrain Ribbon Hat Band & Loop Woven Polyester Sweatband Unlined  Packable / Crushable   Sizes: S, M, L, XL, and XXL; fits true to size.  

(4)
$66.00

…of kick to the standard flat cap style. Made in a summer weight suiting material, so you can enjoy all day long.   Approx. 9 1/2" Diameter 2" Snap Bill/Brim   Made of: 100% Polyester   Lined Bailey Side Pin Snap Bill/Visor   Sizes: S, M, L, XL and XXL  

$63.00
Available Colors:
  • GRAPHITE
  • BASALT

…of the Bailey of Hollywood Lord gives its wearer a confident, refined look.   Approx. 2" Snap Bill/Visor   Made of: 70% Wool 30% Polyester   Made in Italy Bailey Oval Side Pin Woven Ribbon Sweatband Satin Lining   Sizes: S, M, L, XL and XXL; fits true…

$83.00
Available Colors:
  • BLACK
  • CHARCOAL
  • BROWN
  • CAMEL

…4" Center Dent Crown 2 3/4" Curled Brim   Made of: 100% Wool Felt - Stiff Finish   Made in the USA Grosgrain Ribbon Hat Band w/ Side Bow Side Feather Laser Etched Bailey Side Logo Grosgrain Ribbon Trimmed Brim Comfort Sweatband Satin Lining   Sizes: S, M, L, XL and XXL

(2)
$118.00
Available Colors:
  • BLACK

  Made in the USA   The Bailey Darron Wool LiteFelt Pork Pie Hat was created with a handsome telescope crown, making it a style so versatile it can be the finishing touch to any outfit!   Approx. 3 5/8" Telescope Crown 1 5/8" Snap Brim   Made of: 100% Wool…

(4)
$100.00

  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 flared brim for a timeless Aussie/western…

(4)
$92.00
Available Colors:
  • BLACK
  • PECAN

…call us at 1-888-847-4287 for help with sizing. S = 6 3/4 M = 7 L = 7 1/4 XL = 7 1/2 XXL =7 3/4   Made in the USA Are you missing that one hat from your collection? I bet it is the Bailey of Hollywood Heritage Derby. This gorgeous piece is made in the USA and crafted to…

(2)
$110.00
Available Colors:
  • BROWN
  • WHITE
  • BLACK

…you out there.    Approx. 4 1/4" Crown 2 5/8" Brim   Made of:  65% Polyester 35% Cotton   Unlined Padded cotton sweatnand Side eyelets Leather headband with prong back Bailey oval pin Water repellent   Sizes: S, M, L, XL, and XXL; fits true to size.  

(25)
$65.00
Available Colors:
  • BLACK
  • NAVYBLUE
  • CHINO

…from a true quality brand.   Approx. 3 7/8" Teardrop Crown 1 3/4" Snap Brim   Made of: 55% Toyo Straw 45% Polyester    Self Hat Band Cotton Sweatband Bailey Side Pin OR Tag Unlined Packable / Crushable   Size(s): S, M, L, XL and XXL - Fits true to size.  

(23)
$66.00

…Shantung LiteStraw®    Made in the USA Exclusive LiteStraw® Finish - Lightweight & Water Repellent Multi-colored Striped Hat Band w/ Side Bow Bailey Side Pin DRI-LEX® Absorbent Sweatband Bailey Crown Tip Inner Label   Sizes: S, M, L, XL, and XXL; fits true to size.  

$135.00
Available Colors:
  • NATURALBLUE

…construction by Bailey of Hollywood.   Approx. 1 7/8" Sewn Bill/Visor   Made of: 35% Cotton 65% Polyester   Signature 5-Panel Design Water Resistant Wooden Bailey Side Pin Comfort Sweatband Lightweight Fabric Lining   Sizes: S, M, L, XL and XXL; fits true to…

(1)
$50.00
Available Colors:
  • TAN
  • BLACK
  • NAVYBLUE

Bailey metal side pin on the back. The lined interior is comfortable, allowing for a great fit you'll love.   Approx. 2" Pre-Curved Bill   Made of: 50% Wool 50% Polyester   Offset Paneled Pattern Bailey Metal Side Pin Lined   Sizes: S, M, L, XL, and XXL; fits…

$59.00
Available Colors:
  • BROWN

…make this a cap for any man, as long as any man is fit to be comfortable.   Approx. 2" Snap Bill/Visor   Made of: 80% Wool 20% Polyamide   Made in Italy Woven Ribbon Sweatband Satin Lining Bailey Side Pin   Sizes: S, M, L, XL and XXL; fits true to size.  

$90.00
Available Colors:
  • BLACK
  • BROWN

…Approx. 3 3/4" Crown 2 1/2" Brim   Made of: 100% Wool Felt - Lanolux® Finish   Made in the USA Premium Lanolux® Finish - Luxurious Sheen & Soft Feel Leather Hat Band Fine Woven Sweatband "Bailey" Side Pin   Sizes: S, M, L, XL, XXL and XXXL; fits true to size.  

$140.00
Available Colors:
  • BLACK
  • WALNUTBROWN
  • BLUE
  • BLACKMIX

…head cooler and dryer all day long. Approx. 3 3/4" Teardrop Crown 2" Snap Brim   Made of: 100% Shantung LiteStraw®   DRI-LEX® Absorbent Sweatband Japanese Grosgrain Hatband Removable Side Feather Bailey Logo   Size: S, M, L, XL, and XXL; fits true to size.  

(3)
$130.00
Available Colors:
  • NATURALBLACK

…2" Snap Brim   Made of: 100% Toyo LiteStraw® - Supple Feel   Made in the USA Exclusive LiteStraw® Finish - Supple, Shape Retentive & Water Repellent Grosgrain Ribbon Hat Band w/ Side Bow Bailey Side Pin Cotton Sweatband Unlined   Sizes: S, M, L, XL and XXL  

$44.25

…stylish on a summer evening.   Plus the snap-down crown makes sure it never loses its slick shape.   Approx. 1 3/4" Snap Bill/Visor   Made of: 100% Wool   Woven Sweatband Satin Lining Bailey Oval Pin   Sizes: S, M, L, XL and XXL; fits true to size.

(2)
$85.00
Available Colors:
  • BLACK
  • BROWN

  There's just something comforting about the Bernick Wool Blend Baseball Cap from Bailey of Hollywood. Maybe it's the classic buckram supported front panels, maybe it's the comfortable and cushioned sweatband, or maybe it's the adjustable snap strap in the back. Whatever it is, this hat is…

$60.00
Available Colors:
  • OLIVEGREEN
  • BURGUNDY

  Made in the USA   Crafted with an extra wide brim and Bailey's Elite stiffened finish, the new Colver Elite Wool Felt Fedora Hat is a handsome new style for fall and winter. Starting with a classic tear drop crown, the Colver is trimmed with a narrow Japanese grosgrain hat band,…

$163.00
Available Colors:
  • SILVER
  • CHESTNUT

…value.   Approx. 4" crown 2 1/2" snap brim   Made of: 100% Wool Felt - Stiff Finish   Grosgrain ribbon hat band Removable side feather Bailey imprinted on hat band Satin Lining Poly Blend Sweatband   Sizes: S, M, L, XL, and XXL; fits true to size.  

(4)
$120.00
Available Colors:
  • BLACK

  Introducing the Bailey Shupp II Wool Felt Ascot Cap by Bailey. This is a great piece for those that prefer a more form fitted cap. It has side vents to give your head a little bit of ventilation and adds a little extra style without over doing it.   Approx. Round Crown 2" Sewn…

(1)
$65.00

…9 3/4" Length, Flat 10" Width, Flat 1 3/4" Double Snap Bill   Made of: 100% Virgin Wool   Made in Italy Classic Ivy Cap Design Windowpane Plaid Pattern Bailey Side Pin Grosgrain Ribbno Sweatband Smooth Satin Lining   Sizes: S, M, L, XL and XXL; fits true to size.

$85.00

…together in the Gunnar Panama Straw Fedora Hat by Bailey. The innovative 2-toned hat band has been given a western rope feel thanks to the heavy thread topstitching. Blocked and finished in the USA of 100% of Panama straw, this hat is trimmed with a Bailey side pin and DRI-LEX® sweatband for added…

$190.00
Available Colors:
  • TAN

  Made in the USA   Grab and go with the Relik Shantung Straw Fedora Hat by Bailey, a fedora that will keep you cool and protected this summer. Made in the USA of 100% shantung straw, lightweight yet strong, the Relik is finished with LiteStraw® that provides a supple feel, water…

$150.00

…Front Crown 2 3/8" Snap Brim   Made of: 100% Genuine Panama Straw (Brisa Weave)   Handwoven in Ecuador Blocked & Finished in the USA Japanese Grosgrain Hat Band Bailey Side Pin Fine Woven Sweatband Unlined   Size: S, M, L, XL, and XXL; fits true to size.  

$150.00

…  Inspired by nature, the Bailey of Hollywood Spencer Toyo LiteStraw Fedora Hat keeps the rain out and style always on. This toyo design features their exclusive LiteStraw® finish for an amazingly comfortable feel in addition to water repellency. With Bailey's LiteStraw® finish your perception…

(3)
$85.00
Available Colors:
  • NATURAL

…Crown 2" Underwelt Snap Brim   Made of: 100% Wool Felt - Soft & Packable Finish   Made in the USA Grosgrain Ribbon Hat Band Side Feather Printed Bailey Logo - On Side Bow Sweatband Unlined Packable / Crushable   Sizes: S, M, L, XL and XXL; fits true to size.  

(11)
$100.00

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