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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 (52)

Bailey Xxl

1 - 28 of 52 Products
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…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…

$88.00
Available Colors:
  • BLACK
  • CHARCOAL
  • BROWN
  • CAMEL

…Brim   Made of: 100% Wool Felt - Soft & Packable Finish   Made in the USA VHS Exclusive Colors 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.  

(1)
$100.00

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…

$60.00
Available Colors:
  • BROWN

…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

…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.  

(26)
$66.00

…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

…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)
$90.00
Available Colors:
  • BLACK
  • BROWN

…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.

$90.00

…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.  

(6)
$66.00

…Center Pinch Crown 3" Down-Sloping Brim   Made of: 100% Wool   Made in the USA Velour Finish Double-Wrapped Leather Hat Band Bailey Wood-Chip Logo Underwelt Binding On Brim  Dri-Lex Absorbent Sweatband Unlined   Size(s): S, M, L, XL and XXL; fits true to size.  

$170.00
Available Colors:
  • BLACK
  • CAMEL

  Made in the USA   The Renegade® Lexington Wool Felt Western Hat by Bailey features a polished stiff wool felt finish for a crisp and handsome look that won't lose its shape. Crafted with a pinched tear drop crown, the Lexington is finished with a leather tassel hat band and a…

(2)
$94.00

…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.  

(2)
$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

…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)
$120.00
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)
$105.00

  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)
$96.00
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)
$120.00
Available Colors:
  • BROWN
  • WHITE
  • BLACK

…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

…up for evening or dressed down for a casual look. There will be no other cap that fits this nicely on one's head.   Approx. 9" Diameter 2" Sewn Bill/Visor   Made of: 100% Linen   Bailey Side Pin Comfort Sweatband Fabric Lining   Sizes: S, M, L, XL and XXL

(6)
$55.00
Available Colors:
  • BEIGE

…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.  

$95.00
Available Colors:
  • BLACK
  • BROWN

…modern man.   Approx. 4" Crown 2" Snap Brim   Made of: 55% Toyo Straw (Paper) 45% Polyester   Multi-Color Striped Grosgrain Ribbon Hat Band Bailey Side Pin Cotton Sweatband Unlined Packable / Crushable   Sizes: S, M, L, XL, and XXL; fits true to size.  

$56.10
Available Colors:
  • SLATE

…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

…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.  

$56.10
Available Colors:
  • BLUE

…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

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey of Hollywood Blixen Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt® finish gives…

$83.30
Available Colors:
  • RUST

…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.  

$127.50
Available Colors:
  • NATURAL

  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…

(3)
$65.00

…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

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