With the foundation of a long and proud heritage, world-renowned quality, innovation, and fashion forward styling, Bailey Hats of Hollywood continues to be a leader in the western, fashion and casual hat arena for men.

  • Sale! Holland Hats Bailey Chiron Tan

    Bailey Chiron Cotton/Linen Ivy Style Cap

    Bailey Chiron Cotton/Linen Ivy Style Cap

    Colors
    Sizes
    $55.00 $46.75

    Bailey Chiron Cotton/Linen Ivy Style Cap-

    The Bailey of Hollywood Chiron is a classic flat cap boasting a dapper plaid pattern. This cotton and linen blend cap is lightweight and comfortable, perfect for the spring and summer seasons. It is fully lined and finished with a comfort sweatband. The Chiron is part of the Bailey of Hollywood Breed collection; hats that represent a forward-thinking, creative aesthetic.

    Style Ivy Caps & Flat Caps
    Collection Breed by Bailey
    Fabric Cut & Sew, Cotton, Linen
    Material 60% Cotton
    40% Linen
    Crown Flat
    Season Spring/Summer
  • Sale! Holland Hats Bailey of Hollywood Lord Wool Ivy Cap Black

    Bailey of Hollywood Lord Wool Ivy Cap

    Bailey of Hollywood Lord Wool Ivy Cap

    Color
    Standard Sizes
    $75.00 $63.75

    A solid wool classic cap, the Bailey of Hollywood Lord Wool Ivy Cap is a sporty styled wool cap from their Italian Collection, crafted from a soft wool blend. Arriving in a solid patterned material and adorned with a Bailey insignia script hatpin, the Lord is a smart look that goes with so many different styles and visual motifs. That is the calling card of this classic flat cap from Bailey of Hollywood. The Lord features a pair of metal snaps on the brim to keep the front of the crown snug against the bill for that quintessential sleek cap profile.

    SKU 25202
    COLLECTION Est. 1922
    FABRIC Cut and Sew, Wool
    MATERIAL Wool-Polyester-Rayon
    Blend BRIM 1 7/8 inches
    CROWN Ivy
    SEASON Autumn/Winter
    STYLE Ivy Caps & Flat Caps

  • Sale! Holland Hats Bailey of Hollywood Lord Plaid Ivy Cap Black

    Bailey of Hollywood Lord Plaid Ivy Cap

    Bailey of Hollywood Lord Plaid Ivy Cap

    Color
    Standard Sizes
    $75.00 $63.75

    Bailey of Hollywood Lord Plaid Ivy Cap crafted in Italy from a wool blend and finished with a hounds tooth plaid pattern, the Lord Plaid Ivy Cap is a classic cap from the Bailey of Hollywood brand. Details include a satin liner and a grosgrain sweatband.

    SKU 25204
    COLLECTION Est. 1922
    FABRIC Cut and Sew, Wool
    MATERIAL Wool-Polyester-Acrylic
    Blend BRIM 1 3/4″
    CROWN Ivy
    SEASON Autumn/Winter
    STYLE Ivy Caps & Flat Caps

  • Sale! Holland Hats Bailey of Hollywood Lord Nailhead Cap

    Bailey of Hollywood Lord Nailhead Cap

    Bailey of Hollywood Lord Nailhead Cap

    Color
    Standard Sizes
    $75.00 $63.75

    Crafted in Italy, the Bailey of Hollywood Lord Nailhead Cap. It is made with a wool blend that is finished with a striking nailhead pattern. Details include a satin lining and a grosgrain sweatband.

    SKU 25205
    COLLECTION Est. 1922
    FABRIC Cut and Sew, Wool
    MATERIAL 100% Wool
    BRIM 1 3/4 inches
    CROWN Ivy
    SEASON Autumn/Winter
    STYLE Ivy Caps & Flat Caps

  • Sale! Holland Hats Bailey of Hollywood Galvin Solid Wool Cap Brown

    Bailey of Hollywood Galvin Solid Wool Cap

    Bailey of Hollywood Galvin Solid Wool Cap

    Color
    Standard Sizes
    $80.00 $68.00

    Made in Italy, the Galvin Solid Wool Cap is a classic 8/4 cap from Bailey of Hollywood. This traditional newsboy cap is made with a wool blend and features a satin lining and a grosgrain sweatband.

    SKU 25210
    COLLECTION Est. 1922
    FABRIC Cut and Sew, Wool
    MATERIAL Wool-Polyester Blend
    BRIM 2 inches
    CROWN 8-Panel
    SEASON Autumn/Winter
    STYLE Newsboy

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  • Sale! Holland Hats Bailey of Hollywood - Spencer - Made in USA

    Bailey of Hollywood – Spencer – Made in USA

    Bailey of Hollywood – Spencer – Made in USA

    Color
    Sizes
    $78.00 $68.50

    Bailey of Hollywood – Spencer – Made in USA – The Spencer is made with a LiteStraw® finish that is durable, flexible, and water-repellent. It’s universally flattering teardrop crown and 2 3/8″ down-brim provide ample sun protection for those hot summer days. This hat is proudly crafted in the U.S.A.

    Brand Bailey of Hollywood
    Shape Fedora
    Material 100% LiteStraw
    Brim 2 3/8″
    Crown Teardrop
    Season Spring/Summer
    Made in USA Made in USA
    Water Resistant Water Repellent
  • Sale! Holland Hats Bailey of Hollywood Galvin Tweed Cap

    Bailey of Hollywood Galvin Tweed Cap

    Bailey of Hollywood Galvin Tweed Cap

    Color
    Standard Sizes
    $85.00 $72.25

    Bailey of Hollywood Galvin Tweed Cap made in Italy, the Galvin Tweed Cap is crafted with a wool blend tweed fabric. This classic Bailey of Hollywood 8 panel cap boasts a satin lining and a grosgrain sweatband.

    SKU 25211
    COLLECTION Est. 1922
    FABRIC Cut and Sew, Wool
    MATERIAL Wool-Nylon Blend
    BRIM 2 inches
    CROWN 8-Panel
    SEASON Autumn/Winter
    STYLE Newsboy

  • Sale! Holland Hats Bailey Of Hollywood Tino LiteFelt Fedora Black

    BAILEY TINO LITEFELT® FEDORA

    BAILEY TINO LITEFELT® FEDORA

    Colors
    Sizes
    $88.00 $74.88

    BAILEY TINO LITEFELT® FEDORA – The Bailey of Hollywood Tino is made with our famous LiteFelt® finish, a revolutionary treatment process that takes a natural unstiffened premium wool felt hat and makes it water repellent and shape retentive. LiteFelt® adds a tough and indestructible element, combining style and function and is Bailey’s best-selling finish. This hat is our best seller year after year! Laser etched logo. Nailhead detail on Japanese grosgrain. Comfort sweatband. Removable feather. Made in the U.S.A.

    SKU: 7001
    STYLE: Fedora
    COLLECTION: Breed by Bailey
    FABRIC: LiteFelt, Wool Felt
    MATERIAL: 100% LiteFelt
    BRIM: 2″
    CROWN: Center Dent
    SEASON: Autumn/Winter
    MADE IN USA: Made in USA
    WATER RESISTANT: Water Repellent
  • Sale! Holland Hats Bailey Fedora Black

    Litefelt® Fedora By Bailey of Hollywood – Made in USA

    Litefelt® Fedora By Bailey of Hollywood – Made in USA

    Colors
    Sizes
    $90.00 $76.50

    Litefelt® Fedora By Bailey of Hollywood – Made in USA 

    About this Bailey hat-The Bailey of Hollywood Breed group salutes the pioneers of style: the experimenters, the avant garde, the most intriguing troubadours of style. Breed hats are the most directional, stylish and sophisticated hats that Bailey offers. This hat is made with the famous LiteFelt® finish, a revolutionary treatment process that takes a natural unstiffened premium wool felt hat and makes it water repellent and shape retentive. LiteFelt® adds a tough and indestructible element, combining style and function and is their best selling finish. Laser etched logo, nailhead detail on Japanese grograin. Comfort sweatband. Removable feather. 100% wool. Made in the USA.

    Fabric Felt, Litefelt®, Wool, Wool Felt
    Material 100% LiteFelt®
    Brim 2 7/8″
    Crown Pinch Front
    Season Autumn/Winter
    Made in USA Made in USA
    Water Resistant Water Repellent
    Style Fedora
  • Sale! Holland Hats Bailey Galvin 8/4 Style Cap - Made in Italy

    Bailey Galvin 8/4 Style Cap – Made in Italy

    Bailey Galvin 8/4 Style Cap – Made in Italy

    Color
    Sizes
    $102.50 $79.95

    Bailey Galvin 8/4 Style Cap – Made in Italy – Distinct Fashion Pattern. 100% wool cap, Bailey satin lining with matching grosgrain sweatband. Discreet Bailey medallion on back

    Fully and Exquisitely Lined

    Free Same Day Shipping!

  • Sale! Holland Hats Bailey of Hollywood Gangster Fedora

    Bailey of Hollywood Gangster Fedora

    Bailey of Hollywood Gangster Fedora

    Color
    Standard Sizes
    $95.00 $80.75

    The Bailey of Hollywood Gangster Fedora found widespread use and immense popularity among infamous prohibition-era lawbreakers, bootleggers, and bank robbers. Iconic and celebrated crooks such as Al Capone, Bugsy Siegal, and John Dillinger all preferred this fedora style, with its distinctive front pinch and wide brim, and feather accent over a wide grosgrain band and bow. The Bailey of Hollywood interpretation of the Gangster Hat is a classic Fedora with a sleek modern look, and great feel. Experiencing a rejuvenation in popular culture, the Gangster is a timeless fashion piece. Made in the U.S.A.

    SKU 3814
    COLLECTION Est. 1922
    FABRIC Felt, Wool
    MATERIAL 100% Wool
    BRIM 2 1/2 inches
    CROWN Pinch Front
    MADE IN USA Made in USA STYLE Fedora

  • Sale! Holland Hats Bailey of Hollywood Jett Pork Pie Hat

    Bailey of Hollywood Jett Pork Pie Hat

    Bailey of Hollywood Jett Pork Pie Hat

    Color
    Hat Sizes
    $95.00 $80.75

    A Jazzy standard of the hatting world, the Bailey of Hollywood Jett Pork Pie Hat features a classic and classy fur felt construction that demonstrates another meticulously detailed effort by Bailey of Hollywood. Though the hat’s sleek jet nap silk finish and overall smart look initially signified a worldly and social individual, the easily identifiable Pork Pie has been adopted by all kinds of various subcultures and niche enthusiasts since its earliest versions. With a classic telescope crown encircled by the style’s characteristic indentation, the Jett Pork Pie is the definitive example of this famous style.

    SKU: 1451
    COLLECTION: Est. 1922
    FABRIC: Felt, Wool
    MATERIA:L 100% Wool Felt
    BRIM: 2 inches
    CROWN: Telescope
    SEASON: Autumn/Winter
    MADE IN USA: Made in USA STYLE Pork Pie
    COLOR: Black