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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 (21)

Bailey Winters

1 - 21 of 21 Products
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…Made in the USA   Featuring Bailey's proprietary Elite Finish, the Winters Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an unbelievably…

$135.00
Available Colors:
  • ALMOND
  • BLACK

…from summer to fall and winter seamlessly.    Approx. 3 3/4" Pinch Crown 1 3/4" Snap Brim   Made of: 40% Acrylic 40% Toyo Straw (Paper) 20% Polypropylene (i.e. Winter Toyolene Braid)   Color-Blocked Design No Hat Band Micro Bailey Staple Side Pin Cotton Sweatband…

$70.00
Available Colors:
  • FORESTGREEN

…fall and winter with the unique Falconer Cap by Bailey!   Approx. 2 1/2" Crown - Front 3 3/8" Crown - Back 2 1/4" Bill/Brim 2 1/2" Tuckaway Earflap   Made of: 100% Genuine Lambskin Leather   Poet® Collection Cap Military Cadet/Trapper Hybrid Design Bailey Wooden…

$125.00
Available Colors:
  • CHESTNUT

…by Bailey is a handsome new style for fall and winter. The Goldring is crafted in the USA of premium wool LiteFelt® for a soft, packable/crushable and water repellent finish. Its classic pinch crown is adorned with a striped grosgrain ribbon hat band with a fold-over side detail and Bailey micro…

$88.00
Available Colors:
  • NAVYBLUE
  • SILVERBELLY

…thick and warm, perfect for the cooler fall and winter months.    Approx. 11 1/4" Length, Flat   Made of: 35% Cotton 27% Nylon 27% Viscose 7.5% Wool 3.5% Cashmere   Slouchy Rib Knit Beanie Double-Wall Design Bailey Sewn Tab   Size: One Size Fits Most -…

$55.00
Available Colors:
  • BLACK

…right, flying from site to site looking for the right winter headwear to finish of your distinctive cold weather look, you might find yourself sky high in the Vedder from Bailey of Hollywood. The Vedder, a mini trapper from Bailey of Hollywood is a very unique and stylish leather aviator…

$170.00
Available Colors:
  • BRONZE

  The thermostat may be frozen over, but that doesn't mean you have to be. Winter might be the time of 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 is…

$125.00
Available Colors:
  • BLACK

  Get into the fall and winter spirit with the new Kottler Wool Blend Ivy Cap by Bailey! Featuring an oversized plaid pattern in a variety of hues, this cap is crafted of two panels with a slightly extended sewn bill and a wooden Bailey side pin. Keep warm while looking great with the new…

$60.00
Available Colors:
  • HUNTERGREEN
  • OLIVEGREEN

  Made in the USA Introducing the Nock Wool LiteFelt Western Hat by Bailey. Crafted in the USA using their exclusive LiteFelt® finish, the Nock Western is soft, packable/crushable and water repellent making it an excellent outdoor hat. Its stylish, low Hondo (aka tear drop) crown…

$64.00
Available Colors:
  • PUTTY

…  Featuring a lightweight cashmere and wool blend, the Bailey Cole Cashmere & Wool Ivy Cap is a stylish new cap for fall and winter. Expertly crafted in Italy, the Cole Ivy Cap boasts a classic sewn 2-panel design trimmed with a Bailey metallic side pin and a satin lining. Its lightweight…

$95.00
Available Colors:
  • BLACK
  • CAMEL
  • CHARCOAL

…New to the Bailey Galvin design, the Galvin Striped Twill Wool Newsboy Cap features a stylish striped tweed pattern perfect for the season. Featuring the Galvin's classic newsboy design, this cap boasts an 8-panel crown, Bailey back pin and a double snap bill. Great for cool fall and winter months,…

$95.00
Available Colors:
  • CHARCOAL

  Top off your look this autumn and winter with the velvety softness and luxurious sheen of the new Wyman Velvet Newsboy Cap by Bailey. Part of their innovative Breed® Collection of hats and caps, Wyman boasts a more structured 8-panel design complete with a stylish extended bill. Its soft…

$60.00
Available Colors:
  • BLACK
  • BURGUNDY
  • NAVYBLUE

  Bailey introduces the Fernales Fedora that brings that classic style with you from your fall/winter hat into spring/summer style.   Aprrox. 4" Crown 1 3/4" Pre-Snap Brim   Made of: 100% Palm Straw   Unlined Bailey side pin Grosgrain ribbon band   …

$51.00
Available Colors:
  • NATURAL

…not feature a center top button. For a finishing touch, a small wooden Bailey side pin is placed at the cap's left side. Perfect for fall and winter, the Salko Cotton Newsboy Cap has a singular look you need to add to your Bailey cap collection!    Approx. 9 5/8" Length, Flat 10" Width,…

$80.00
Available Colors:
  • DENIMBLUE

  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,…

$140.00
Available Colors:
  • BLACK

…the hat's crown when not in use. Bailey's exclusive LiteFelt® finish gives the hat its soft and packable/crushable nature while also making it water repellent. Ideal for colder (and wetter) fall and winter months, the Joe Eder Wool LiteFelt Western Hat by Bailey has the functionality you need in…

$54.40
Available Colors:
  • SERPENT
  • BLACK

  The new Smit Tweed Wool Ivy Cap by Bailey features their modern, contoured 5-panel design for an exceptional fit. Adorned with a minimal Bailey staple pin, the Smit has a clean and updated look. Perfect for fall and winter, the Smit Tweed Ivy will keep you warm AND in style.    …

$63.00
Available Colors:
  • BLACK
  • CAMEL
  • NAVYBLUE

…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

…the finest virgin wool, the new Bailey Lord Windowpane Plaid Wool Ivy Cap is a great new addition to their Lord cap collection, including the Solid and Herringbone versions. Its classic 2-panel sewn design is sleek and handsome; adorned only with a small Bailey metallic side pin. Its relatively…

$68.00

…the new Galvin Houndstooth Wool Blend Newsboy Cap by Bailey has arrived! Featuring a classic houndstooth tweed pattern, the Galvin Houndstooth Newsboy is also crafted in Italy of the finest materials. Perfect for autumn and winter, this cap is sure to become one of your favorites! …

$72.25
Available Colors:
  • BLACK
  • BROWN

…winter.    See the Bailey Lord Cap's Solid version or classic Herringbone version to complete your collection!   Made of: 25% Wool 35% Polyester 40% Acrylic   Made in Italy Classic Ivy Cap Design Windowpane Plaid Pattern Bailey Side Pin Grosgrain Ribbon Sweatband…

$63.75
Available Colors:
  • BLACK
  • BROWN
  • GREEN

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