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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 (161)

Bailey Hats

1 - 30 of 161 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…

$60.00

…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

…Crown your restless spirit with the new Ashmore Wool LiteFelt Fedora Hat by Bailey! Part of their Poet® Travel Collection inspired by the spirit and grit of the Old American West, Ashmore is crafted in the USA using Bailey's exclusive wool LiteFelt® that is soft, packable/rollable, water repellent…

$105.00
Available Colors:
  • BLACK
  • BURGUNDY

  Made in the USA The Curtis Wool Felt Safari Fedora Hat is one of the most practical hats in the Bailey line. The classically designed safari fedora repels water and oil based spills. It is breathable, and durable and can be packed for ease of travel.    Approx. 4" Center…

$90.00

…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 down-sloping brim characterize this elegant fedora hat. Finished with a Japanese grosgrain hat band, small Bailey side pin, fine woven sweatband and fully…

$135.00

…Long Teardrop Fedora Hat by Bailey also boasts a distinctive polished felt finish, resulting in a lustrous finish and silky felt texture. Trimmed with a deluxe Japanese grosgrain ribbon hatband and small Bailey side pin, the Criss Wool Felt Long Teardrop Fedora Hat is a gorgeous addition to your hat

$120.00

…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…

$88.00

…the Bailey of Hollywood Vito Toyo Straw Braid Trilby Fedora Hat which has a great combination of colors. The pattern on the crown creates the appearance of a hat band without one actually being present. This hat is also crushable so you don't have to worry about someone picking up the hat and…

$70.00

…blocked design, the Grimet Toyo Braid Straw Trilby Fedora Hat by Bailey is an eye-catching, sleek style. Crafted of extra fine braided Toyo straw for a lightweight and packable finish, Grimet keeps the details simple with only a small Bailey staple side pin. Its stingy snap brim can be worn snapped…

$70.00
Available Colors:
  • CHARCOAL

…  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

…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  

$100.00
Available Colors:
  • BLACK
  • CORDOVABROWN

…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…

$140.00
Available Colors:
  • NATURAL

…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

  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…

$60.00
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…

$60.00
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…

$68.00
Available Colors:
  • OLIVEMIX
  • BEAVER

  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…

$44.00
Available Colors:
  • BLACK

  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.  …

$65.00
Available Colors:
  • TANBROWN

…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

$100.00
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.     …

$70.00
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…

$68.00
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…

$65.00
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…

$70.00
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…

$72.00
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. …

$150.00
Available Colors:
  • NATURAL

…braided waxed cord hat band, Sturges is finished with a Bailey-branded leather closure, an underwelt brim and adjustable sweatband. Take on the outdoors with confidence while wearing your handsome and functional Sturges LiteFelt Fedora, part of Bailey's rugged Poet® collection of hats.    …

$105.00

… 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

…flair, the Derian Toyo Straw Outback Hat by Bailey features their exclusive new Endura finish which helps the hat maintain its shape even after getting wet. Lightweight, pliable and completely packable, Derian is finished with a pattern woven hat band and Bailey side pin. Inside, an absorbent…

$100.00

Bailey of Hollywood Noble Fur Felt Fedora Hat has a crown you don't see every day. This piece is a great hat to add to your collection because it is unique and is made to perfection.   Approx. 4" Crown 2 3/4" Brim   Made of: 100% Fur Felt   Made in the USA Grosgrain Hat

$350.00

…Introducing the Fernley Shantung LiteStraw Fedora Hat by Bailey of Hollywood. Made of supple shantung straw, this style boasts Bailey's exclusive LiteStraw® technology for a soft and water repellent finish. Perfect for those who prefer wide-brimmed hats but hate being weighed down by heavier straw,…

$120.00

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