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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 (166)

All Bailey Hats

1 - 30 of 166 Products
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…Look no further than the striking Tasmin Panama Straw Fedora Hat by Bailey! All genuine panama hats, including the Tasmin, are handwoven by artisans in Ecuador; the Tasmin was then blocked and finished in the USA by expert Bailey craftsmen. The Tasmin's multi-color braided inlaid crown insert…

$136.00
Available Colors:
  • MULTI

…  The Bailey Toyo Straw Fedora Hat is part of ále by Alessandra's new line for spring and summer. Featuring a classic fedora design adorned with a paisley bandana hat band, the Bailey has a unique look perfect for casual wear. Rest easy knowing you are protected not only by the hat's wide brim…

$68.00

  A classic bucket hat from Bailey, the Clapcott Rain Bucket Hat has a few added features for extra functionality. Its water resistant fabric helps keep you dry while the back of the crown boasts a storage zipper to handily store your cash, ID or credit cards. Inside, the Clapcott is fully…

$51.00
Available Colors:
  • BLACK

  Finally a beanie cap worthy of calling itself a Bailey – introducing the new Frost Knit Beanie Hat! Made of a soft blend including cotton, wool and cashmere, the Frost Beanie Hat boasts a slouchy fit in a classic rib knit. Its double-wall design makes this beanie extra thick and warm, perfect for…

$46.75
Available Colors:
  • BLACK

  The Marr Wool Fedora Hat from Bailey of Hollywood is sure to become a staple of any wardrobe. The colorful grosgrain hat band is incredibly sophisticated, with the lined interior and heavy sweatband make for a most comfortable fit. Add it to your wardrobe today!   Approx. 4" Pinched…

$51.00
Available Colors:
  • OLIVEGREEN

…thick sweaters and bulky coats, however you can stay fashionable in the frigid freeze thanks to Bailey of Hollywood. The Vega is a trapper style cap with faux fur earflaps. The Vega Leather Trapper Hat is fabulously comfortable and an edgy statement on the road. So, hop on your hog and strap on…

$106.25
Available Colors:
  • BLACK

…with Bailey's fashion forward Jett Nap Finish. These premium wool felts are crafted with Bailey's exclusive blend of 100% virgin wool fibers and a unique silk-like finish, adding a luxurious sense and character. The hat comes fully lined in satin. 4" crown and 2" snap-brim. 18 lignes gros-grain hat

$85.00
Available Colors:
  • BLACK

  Get ready for summer with the Freddy Braid Fedora Hat from Bailey! This packable, crushable hat is perfect for travel, and features alightweight  breathable unlined interior with a cotton twill sweatband. Best of all, the heathered build is incredibly comfortable!   Approx. 4"…

$65.00
Available Colors:
  • BLACK
  • RUST
  • STONE

…and unequaled 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, XXL and XXXL  

$85.00
Available Colors:
  • BLACK
  • CORDOVABROWN

…in Bram Stoker's Dracula. The jet nap finish on the wool felt modernizes this sleek derby sleek. Made of: 100% Premium Wool Felt Approx. 4 1/4" crown Approx. 1" brim Bailey side pin Lined Side Feather Grosgrain hat band Note: Lining can be different than what is pictured.

$93.50
Available Colors:
  • BLACK
  • HEMLOCK

…option for those looking for a hat with the look of straw, without the hassle straw hats require. What's not to love?    Approx. 3 7/8" Pinch Crown 2" - 2 1/8" Snap Brim   Made of: 100% Polypropelene   Grosgrain Hat Band Bailey Staple Side Pin Cotton Twill Sweatband…

$55.25
Available Colors:
  • GRAPHITE
  • NATURAL
  • NAVYBLUE
  • RED

…loose. Made in the USA Introducing the Alamo Western Hat by Bailey. This is a great piece to add to your collection. The style cattleman crown mixed with the diamond stud accents on the leather hat band create the perfect classic look to wear just about anywhere.     …

$70.00
Available Colors:
  • BLACK

  Combining toyo straw (paper) and thermo, the Bailey Elliot Straw Fedora Hat offers a breezy option for spring and summer. Lightweight and stylish, the Elliot features a pinch front crown, narrow grosgrain ribbon hat band and a stingy, pre-snapped brim. Don't sweat it this spring/summer, just…

$51.00
Available Colors:
  • NATURAL
  • NAVYBLUE

Made in the USA. An excellent quality 4X virgin wool and imported angora felt blend, the Lightning Western from Bailey is the classic cowboy hat. With it's self band with buckle, you too can be riding off into the sunset in the ultimate in American styling. Approx. 4 3/4" Cattleman Crown 4"…

$110.50
Available Colors:
  • BONE

…Trigger Western Hat by Bailey. This is another great example of the perfect look. The hat band blends with the hat which causes the minature belt buckle to truly shine.   Approx. 4 1/4" Cheyenne Crown  4" Brim   Made of: 100% Wool Felt   Wool Felt Hat Band Lined Metal…

$70.00
Available Colors:
  • BLACK

…Western Hat by Bailey. This cowboy hat is equpped with a dri-lex sweatband to make sure that if you are getting a little hot your hat isn't going to show proof of that happening.   Approx. 4 1/2" Cheyenne Crease Crown  4" Brim   Made of: 100% Wool Felt   Leather Hat

$70.00
Available Colors:
  • BLACK

…Dillinger Western Hat by Bailey. I bet you don't have a top hat quite like this one. This is a great mix between the old west and a classic top hat look.    Approx. 5" Flat Top Crown  4 1/2" Brim   Made of: 100% Wool Felt   Lined Grosgrain Hat Band Leather…

$100.00
Available Colors:
  • BLACK

  Made in the USA Introducing the Jericho 3x Western Hat by Bailey. This piece is truly gorgeous. The hat band was created with pieces of leather attached to one another by three metal accent links on the front. The inside is lined to make sure it will keep you warm during those…

$95.00
Available Colors:
  • MOLE

…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 perfection. The colors are great and they…

$85.00
Available Colors:
  • BROWN
  • WHITE
  • BLACK

…Tessier Panama Straw Fedora Hat by Bailey will add distinctive style to your look this spring and summer! Like all genuine panama hats, the Tessier's body was artfully handwoven in Ecuador then blocked and finished in the USA by master craftsmen. The resulting hat is lightweight, supple and…

$136.00

…Collection of hats and caps. The Maddow's uniquely worn finish is achieved by dyeing then hand-bleaching each hat for a singular gradient finish that adds style and personality. Crafted of Bailey's exclusive shantung LiteStraw®, the Maddow is lightweight, supple and water repellent - all functions…

$85.00
Available Colors:
  • BLACK

…eye-catching custom hat band that layers cording trim and is finished with a smooth leather closure laser-engraved with the Bailey logo. Its soft brim measures about three inches for great coverage, while inside the Rhode boasts an adjustable sweatband for a custom and comfortable fit. All this in a…

$84.15
Available Colors:
  • BLACKMIX

Made in the USA The Bailey Guthrie is made of a new softening and finishing technology for Shantung Straw which creates an incredibly comfortable and flexible fit. As an added bonus, this is one of the few straw hats that is actually water resistant. The hat comes with the Dri-Lex moisture…

$97.75
Available Colors:
  • NATURALBLACK

…Western Hat by Bailey. This is the classic black western hat of your dreams. It's sleek and stylish and will go with just about anything. You can't go wrong with this piece.   Approx. 4 1/2" Cattleman Crown  4" Brim   Made of: 100% Wool Felt   Ribbon Hat Band Lined…

$72.00
Available Colors:
  • SILVERBELLY
  • BLACK

… Made in the USA Introducing the Navarro Western Hat by Bailey. This is a great hat for the true journey man. This piece will keep its shape throughout your trip and will keep you protected along the way. The hat band is created with swirled leather material to give a truly artistic…

$72.00

…fits a little loose. Made in the USA   Introducing the Cavalry II Western Hat by Bailey. Whether you are going for the Union Blue or Conferdate gray you have both options with this hat. It is very stiff and sturdy so you won't have to worry about it being flimsy while you are…

$80.00

  Made in the USA Introducing Bailey's Konrath Shantung LiteStraw Fedora Hat. This is a gorgeous straw fedora crafted of premium shantung straw and boasts Bailey's exclusive LiteStraw® for a lightweight, supple and water resistant finish. You can't go wrong with this piece. …

$127.50
Available Colors:
  • NATURAL

…beauty was obviously his sun hat - he still needed protection for the sun - and he still needed to look good doing it.   Approx. 4" Teardrop Crown 2 3/8" Brim Made of: 100% Genuine Panama Straw (Cuenca Weave)   Grosgrain Ribbon Hat Band Bailey Side Pin Woven Polyester…

$123.25

…the best, like the Stansfield Panama Straw Fedora Hat from Bailey! This American-made hat is made of fine, reliable panama (toquila palm) straw, complete with a leather hat band and woven detail wrapping around the crown. Quality matters, and Bailey knows that!   Approx. 3 3/4" Teardrop…

$160.00
Available Colors:
  • NATURAL

  Introducing the Bailey Tennessee Fedora Hat. This is a great lightweight summer hat to keep you cool and protected from the sun at the same time. The brim and the crown are two different colors but the plaid hat band make them sync perfectly together. You can't go wrong with this piece.  …

$55.25
Available Colors:
  • TANBROWN

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