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 Cole Cashmere Cap - Made in Italy

    Bailey Cole Cashmere Cap – Made in Italy

    Bailey Cole Cashmere Cap – Made in Italy

    Colors
    Sizes
    $116.00 $89.95

    Bailey Cole Cashmere Cap – Made in Italy – 50% Cashmere-50% Virgin Wool, Traditional Ivy Style Shape, Discreet Bailey Medallion on Back, Fully Lined.

    Free Same Day Shipping!

  • 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 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

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  • 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 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 Stockton Premium Ivy Leather Cap

    Bailey Stockton Premium Ivy Leather Cap

    Bailey Stockton Premium Ivy Leather Cap

    Colors
    Sizes
    $129.50 $99.00

    Bailey Stockton Premium Ivy Leather Cap

    Premium top grain smooth leather, very soft.

    Bailey Medallion on side

    Designer fashion backstrap with discreet buckle on back

    Duel Snaps on peak for alternate fashion styles.

    Quilted lining

    Free Same day Shipping

     

  • 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

  • Sale! Holland Hats Bailey of Hollywood Vega Aviator Black

    Bailey of Hollywood Vega Aviator

    Bailey of Hollywood Vega Aviator

    Color
    Standard Sizes
    $125.00 $106.25

    The thermostat may be frozen over, but that doesn’t mean you have to be. Winter might be the time for thick sweaters and bulky coats, however you can stay fashionable in the frigid freeze thanks to Bailey of Hollywood. The Bailey of Hollywood Vega Aviator is a trapper style cap with faux fur earflaps, and ideal for windy excursions. The Vega is fabulously comfortable and an edgy statement on the road.

    SKU: 25105
    COLLECTION: _poet__depr
    FABRIC: Leather
    MATERIAL: Leather-Polyester Blend
    CROWN: Wrapped
    SEASON: Autumn/Winter STYLE Trapper
    COLOR: Black

  • Sale! Holland Hats Baily of Hollywood Taxten Cap

    Baily of Hollywood Taxten Cap

    Baily of Hollywood Taxten Cap

    Color
    Standard Sizes
    $100.00 $85.00

    The Baily of Hollywood Taxten Cap is a classic leather-paneled ivy cap with the casual appeal and presence of a true old-fashioned Sunday driving cap. On the interior, a finely woven grosgrain sweatband nicely accents custom Bailey lining, for a surprisingly rich experience. Continuing with this classic shape and style, Bailey of Hollywood has done it again with the rugged sheepskin leather feel of the Taxten, a cap that loudly and proudly declares your casual ambitions from the highest fashion perch.

    SKU: 25102
    COLLECTION: _poet__depr
    FABRIC: Leather
    MATERIAL: 100% Leather
    BRIM: 2 inches
    CROWN: Paneled
    STYLE: Ivy Caps & Flat Caps
    COLOR: Brown

  • Sale! Holland Hats Bailey of Hollywood Brandt Fedora Black

    Bailey of Hollywood Brandt Fedora

    Bailey of Hollywood Brandt Fedora

    Color
    Standard Sizes
    $120.00 $102.00

    The Bailey of Hollywood Brandt Fedora is a classic pinch-front fedora with a casual turn-down brim and a leather two-tone band. Bailey® continues its long tradition of excellence and innovation with their Lanolux® line. These hats are made in the USA from foreign and domestic components. From 100% virgin wool of the finest microns with a fur felt finish, Lanolux® employs a unique sueding process to create a lightweight, packable, and luxurious material.

    SKU 37158
    COLLECTION _poet__depr
    FABRIC Lanolux®, Wool, Wool Felt
    MATERIAL 100% Lanolux Wool
    BRIM 2 1/2 inches
    CROWN Center Dent S
    EASON Autumn/Winter
    MADE IN USA Made in USA STYLE Fedora

  • 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