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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 (170)

Bailey Hats

1 - 28 of 170 Products
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  Please Note: Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band. Welcome to today's hot new look in an amazingly soft, packable, and comfortable sewn braid! The Bailey of Hollywood Billy is a top selling topper with a stingy…

(22)
$55.00

…Shantung LiteStraw Fedora Hat boasts Bailey's exclusive LiteStraw® finish for a supple feel and added water repellency. Enjoy the handsome look of the Anderson without the stiffness or extensive care of other straw hats. The Anderson features a center fold overlay hat band, side bow, side feather…

$102.00
Available Colors:
  • NATURAL

…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…

$120.00
Available Colors:
  • BLACK

…This style no longer ships with a Bailey side pin. Instead, this style now has a small printed Bailey logo on the side bow.    Made in the USA The Tino Wool Felt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines traditional craftsmanship…

(8)
$95.00

  Stay stylish with the Noakes Toyo Straw Fedora Hat from Bailey. This light-weight hat features a simple, almost minimalist design, made of durable, comfortable toyo straw, complimented by a single Bailey side label. It's all tied together by a solid stripe of color wrapping around the…

$70.00
Available Colors:
  • NATURAL
  • BROWN

… 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…

$88.00

…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  

(4)
$110.00
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
  • BLUE

…USA   The Cutler is a most excellent and stylish Cuenca weave Panama. This beauty from Bailey is the perfect casual summer fedora. It comes complete with a stunning leather band and Bailey hat pin.     Approx. 4" Crown 2 7/8" Pre-snap Brim   Made of: 100% Genuine Panama…

(4)
$123.25
Available Colors:
  • NATURAL

…cool-looking when you're wearing the Stanley Fedora Hat from Bailey. This well-made fedora features a stiffened, dyed braid, a matching woven hat band with a Bailey metal side pin, and a comfortable cotton twill sweatband. If you want to turn heads, this hat is one great look!   Approx. 4"…

$80.00
Available Colors:
  • DARKNATURAL

…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

$88.00
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…

$45.00
Available Colors:
  • OLIVEGREEN

…the Palisade Wool LiteFelt Western Hat by Bailey. The hat band alone will make this hat stand out from the rest. The leather is inverted at various points along its length to create a unique braid pattern while the smooth sections feature metal studs. Bailey's exclusive LiteFelt® finish make the…

$88.00
Available Colors:
  • OLIVEMIX
  • BEAVER

  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…

$45.00
Available Colors:
  • BLACK

…Handwoven in Ecuador, Finished in the USA   Quality matters, like with the Parson Panama Straw Fedora Hat from Bailey. This fine hat features a thin cotton herringbone hat band, as well as a contrast color bound edge around the brim. This USA-made fedora is of the highest quality! …

$170.00
Available Colors:
  • NATURAL

…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

…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!   Approx. 3 1/2" Telescope Crown 3…

(2)
$115.00
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.  …

$48.75
Available Colors:
  • TANBROWN

…The new Lanth Polished Wool Felt Fedora Hat by Bailey boasts luxurious polished wool for incredible softness and a lovely sheen while remaining completely packable. Its classic tear drop crown design is trimmed with a wool felt hat band, micro Bailey staple side pin, comfort sweatband and custom…

$114.75
Available Colors:
  • OXBLOOD
  • 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

$110.00
Available Colors:
  • BLACK

…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.     …

$88.00
Available Colors:
  • BLACK

  Made in the USA Introducing the Recoil Wool LiteFelt Western Hat by Bailey. Accented with a stylish leather hat band trimmed with feathers, this style is finished with a flared brim for a quintessentially western look. Its exclusive LiteFelt® finish makes the Recoil Western both…

$88.00
Available Colors:
  • FALLBROWN

…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

…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…

$92.00
Available Colors:
  • BLACK

…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…

(1)
$88.00
Available Colors:
  • SILVERBELLY
  • BLACK

  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

…USA   The Bailey Reinsman Wool Felt Derby Hat is a classic derby style with a slight Western touch in the shape of its flared upturned brim. Its round crown and upturned brim are trimmed in classic grosgrain ribbon and finished with a Bailey spur side pin. The hat's interior boasts an…

$76.50
Available Colors:
  • PECAN

  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…

$100.00
Available Colors:
  • MOLE

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