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Bailey of Hollywood Shupp II 3828 - Grey Mix Hats

Bailey of Hollywood Shupp II 3828 - Grey Mix Hats

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The Shupp II is a wool felt hat with an ascot crown and blocked cap. more

$59.95

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(175,000+)
Bailey of Hollywood Shupp II 3828 - Black Hats

Bailey of Hollywood Shupp II 3828 - Black Hats

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The Shupp II is a wool felt hat with an ascot crown and blocked cap. more

$59.95

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(175,000+)
Best Seller
Bailey of Hollywood Shupp II 3828 - Brown Mix Hats

Bailey of Hollywood Shupp II 3828 - Brown Mix Hats

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The Shupp II is a wool felt hat with an ascot crown and blocked cap. more

$59.95

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(175,000+)
Bailey of Hollywood - Cudmore (Whiskey) Caps

Bailey of Hollywood - Cudmore (Whiskey) Caps

Give your look a Western-inspired flair with the modernity and edge of the Cudmore fedora from Bailey of Hollywood! ; Panama and suede hat with grad crown. ; Call out print or fabric feature (ie water-repellant) ; Woven horse hair band. Real fur: dyed,... more

$109.99

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Men's Cabbie Newsboy Ascot Herringbone Wool Blend Ivy Hat

Men's Cabbie Newsboy Ascot Herringbone Wool Blend Ivy Hat

KBW-317 BLK L/XL more

$9.99

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Brown Oversized Herringbone Wool Blend Applejack Newsboy Ascot Cabbie Ivy Hat

Brown Oversized Herringbone Wool Blend Applejack Newsboy Ascot Cabbie Ivy Hat

KBW-320 BRN L/XL more

$9.99

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Wool Blend Plaid Ivy Hat Golf Driving Ascot Winter Flat Cabbie Newsboy Debonair

Wool Blend Plaid Ivy Hat Golf Driving Ascot Winter Flat Cabbie Newsboy Debonair

KBL-105 DGY S/M more

$12.99

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Bailey of Hollywood Men's Mannes Braided Fedora Trilby Hat Hat, Brown/Multi, S

Bailey of Hollywood Men's Mannes Braided Fedora Trilby Hat Hat, Brown/Multi, S

Street-wise and ready for action, the bailey of Hollywood Mannes hat is one slick straw fedora, perfect for any scene or happening. This snap-brim braided straw hat is malleable and packable for traveling convenience, and wonderfully eye-grabbing for... more

$49.99

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Bailey of Hollywood Men's Waits Braided Pork Pie Hat Hat, Black, X-Large

Bailey of Hollywood Men's Waits Braided Pork Pie Hat Hat, Black, X-Large

The Bailey of Hollywood waits is a smooth and sleek braided pork pie with a traditional telescoping crown, a grosgrain ribbon hatband, and a stingy upturned brim. more

$59.99

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Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, -black/charcoal multi, Large

Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, -black/charcoal multi, Large

The Mannesroe fedora in bailey's braid collection is a bold yet stylishly sophisticated for the summers evening activities. The multi colored pattern gives this fedora an eye catching appeal and before you know it all of your friends will be asking... more

$49.99

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Men's Bailey Western Fender Straw Cowboy Hat - Toyo Tea Stained Hats

Men's Bailey Western Fender Straw Cowboy Hat - Toyo Tea Stained Hats

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The Fender Straw Cowboy Hat from Bailey Western will protect you from the sun in style. It has a brick crown, a 4" brim, and an adjustable leather band with metal accents. Brick crown Adjustable leather band 4" brim Metal accents. more

$49.95

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(175,000+)
Men's Bailey Western Cavalry II - Silver/Grey Hats

Men's Bailey Western Cavalry II - Silver/Grey Hats

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From the Frontier Collection, this cowboy hat is designed with a pinch front crown and 3.5" brim. more

$79.95

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Men's Bailey of Hollywood Hooper Fedora 81710BH - Earth Hats

Men's Bailey of Hollywood Hooper Fedora 81710BH - Earth Hats

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Stay on the right side of fashion with the contemporary Bailey of Hollywood Hooper Fedora. Featuring a teardrop crown with a gradient pattern, this hat rounds off a smart look. Gradient pattern Teardrop crown with toyolene construction 1¾" snap brim... more

$69.95

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(175,000+)
Men's Bailey Western Cavalry II - Navy Hats

Men's Bailey Western Cavalry II - Navy Hats

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From the Frontier Collection, this cowboy hat is designed with a pinch front crown and 3.5" brim. more

$79.95

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Bailey Western Rowan Straw Hat - Khaki Cowboy Hats

Bailey Western Rowan Straw Hat - Khaki Cowboy Hats

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The Rowan Straw Hat isn't your average buckaroo hat. This beauty has been built with a fine woven straw and shaped with a porkpie top crown. It is adorned with a hand braided leather band and silver rustic buckle, and topped off with a gorgeous... more

$99.95

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Men's Bailey Western Truckton Cowboy Hat - Black Hats

Men's Bailey Western Truckton Cowboy Hat - Black Hats

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Express your Western pride with the Truckton Cowboy Hat from Bailey Western. It comes with a tall, center-creased crown, a wide scoop brim, a two-tone woven leather band, and a spur pin. Wide scoop brim Tall, center-creased crown Accented by a simple... more

$94.95

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Men's Bailey Western Truckton Cowboy Hat - Tan Mist Hats

Men's Bailey Western Truckton Cowboy Hat - Tan Mist Hats

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Express your Western pride with the Truckton Cowboy Hat from Bailey Western. It comes with a tall, center-creased crown, a wide scoop brim, a two-tone woven leather band, and a spur pin. Wide scoop brim Tall, center-creased crown Accented by a simple... more

$94.95

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Bailey Western Roderick Cowboy Hat - Brown Cowboy Hats

Bailey Western Roderick Cowboy Hat - Brown Cowboy Hats

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Amp up your look with Bailey Western's Roderick Cowboy Hat. A trendy rodeo crown gives this hat a masculine edge. The leather band coupled with a buckle detail gives this woolen hat a visually appealing look. Rodeo crown 4 1/4" brim Leather band with... more

$94.95

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Bailey Western Pro 5X Cowboy Hat - Brown Hats

Bailey Western Pro 5X Cowboy Hat - Brown Hats

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Flaunt an iconic country look with Bailey Western's Pro 5X Cowboy Hat. The classic cattleman crown and 4" brim create the image of a true cowboy. A matching band and three-piece metal buckle wrap the base of the crown for a clean look that will... more

$229.95

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Men's Bailey of Hollywood Waits 81810 - Sand Hats

Men's Bailey of Hollywood Waits 81810 - Sand Hats

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This porkpie hat features a telescope crown, a 1 5/8" snap brim, and a wide ribbon band with wood chip logo plaque. more

$69.95

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Men's Bailey of Hollywood Vito 25331 - Black Mix Hats

Men's Bailey of Hollywood Vito 25331 - Black Mix Hats

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This classic and sophisticated braided fedora from the Breed collection features a teardrop crown and a 1 5/8" snap brim. more

$69.95

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Men's RENEGADE by Bailey Western Calico Cowboy Hat - Camel Hats

Men's RENEGADE by Bailey Western Calico Cowboy Hat - Camel Hats

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The Calico Cowboy Hat is packable, crushable, water repellent, and stain resistant! With a low Hondo crown and a 3.5" relaxed brim shape, a feathered notch adorns the left side of this renegade style. Water reppelant Crushable Stain-resistant Hondo... more

$79.95

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Men's Bailey of Hollywood Derby 3816 - Brown Hats

Men's Bailey of Hollywood Derby 3816 - Brown Hats

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The Derby is a wool felt hat with a derby crown and a 2 1/8" roll brim with binding. more

$94.95

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Men's Bailey of Hollywood Tino 7001 - Navy Hats

Men's Bailey of Hollywood Tino 7001 - Navy Hats

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LiteFelt® hats combine traditional artisanship with today's leading technology to produce a revolutionary water repellent hat in 100% wool felt. Soft and packable, with remarkable memory, LiteFelt® hats always spring back to their original shape. This... more

$79.95

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Men's Bailey of Hollywood Brooks 22721 - Sepia Hats

Men's Bailey of Hollywood Brooks 22721 - Sepia Hats

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The Panama hat is hand woven in Ecuador. The art of hat weaving has been inherited from their Inca ancestors and passed from generation to generation. Fibers used to weave the Panama hat are from the Toquilla plant. Featuring a teardrop crown and a 2... more

$139.95

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Men's Bailey of Hollywood Werbow 25136 - Distressed Brown Hats

Men's Bailey of Hollywood Werbow 25136 - Distressed Brown Hats

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Baseball Trapper Outer: 100% Leather; Inner: 100% Fur; Lining: 55% Cotton, 30% Polyester, 15% Linen. more

$174.95

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Men's Bailey of Hollywood Elliott 81652 - Navy Hats

Men's Bailey of Hollywood Elliott 81652 - Navy Hats

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The Elliott hat captures colorful elegance and the luxury of simplicity. Features a center dent crown and a 2" pre-snap brim. more

$59.95

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Bailey Western Supreme - Buckskin Hats

Bailey Western Supreme - Buckskin Hats

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The Supreme features silver hardware, a 4 1/4" Cheyenne crown, and a 4" brim. more

$309.95

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Men's Bailey of Hollywood Hanson 63112 - Natural/Blue Print Hats

Men's Bailey of Hollywood Hanson 63112 - Natural/Blue Print Hats

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LiteStraw® is a revolutionary new finishing technology that takes traditionally hard straw headwear and softens it to create a supple, casual hat that provides malleability and flexibility. Combined with a water repellant finish and Dri-Lex® sweat... more

$109.95

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Men's Bailey of Hollywood Rumsen 25107 - Black Aviator Hats

Men's Bailey of Hollywood Rumsen 25107 - Black Aviator Hats

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This aviator style from Bailey has fur on the sides and a rim that flips out. The sides hang down over your ears for extra warmth but can also be buckled on top of the hat. This hat will have you feeling and looking good. more

$169.95

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Men's Eddy Bros. Calaboose Cowboy Hat - Black Hats

Men's Eddy Bros. Calaboose Cowboy Hat - Black Hats

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The Calaboose Cowboy Hat from Bailey Western has a cassidy crown shape, a faux leather band with silver accents, and a chin cord to make sure that you never lose it. Its wide brim shields you from the sun, and gives it a classic western look. Faux... more

$39.95

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100% Genuine Leather Dark Brown Mens Ivy Hat Golf Driving Ascot Flat Cabbie Newsboy

100% Genuine Leather Dark Brown Mens Ivy Hat Golf Driving Ascot Flat Cabbie Newsboy

KBL-108 DBR L/XL more

$19.99

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Bailey of Hollywood Men's Waits Braided Pork Pie Hat Hat, Black, S

Bailey of Hollywood Men's Waits Braided Pork Pie Hat Hat, Black, S

The Bailey of Hollywood waits is a smooth and sleek braided pork pie with a traditional telescoping crown, a grosgrain ribbon hatband, and a stingy upturned brim. more

$59.99

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Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, Overcast, S

Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, Overcast, S

The mannesroe fedora in bailey's braid collection is a bold yet stylishly sophisticated for the summers evening activities. The multi colored pattern gives this fedora an eye catching appeal and before you know it all of your friends will be asking... more

$48.00

FREE shipping

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Bailey of Hollywood Men's Mannes Braided Fedora Trilby Hat Hat, -brown/multi, Large

Bailey of Hollywood Men's Mannes Braided Fedora Trilby Hat Hat, -brown/multi, Large

Street-wise and ready for action, the bailey of Hollywood Mannes hat is one slick straw fedora, perfect for any scene or happening. This snap-brim braided straw hat is malleable and packable for traveling convenience, and wonderfully eye-grabbing for... more

$51.00

FREE shipping

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Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, -black/charcoal multi, X-Large

Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, -black/charcoal multi, X-Large

The Mannesroe fedora in bailey's braid collection is a bold yet stylishly sophisticated for the summers evening activities. The multi colored pattern gives this fedora an eye catching appeal and before you know it all of your friends will be asking... more

$49.99

FREE shipping

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Bailey of Hollywood Men's Salem Fedora Trilby Hat Hat, Black, S

Bailey of Hollywood Men's Salem Fedora Trilby Hat Hat, Black, S

A tried and true bailey classic toyo braid, featuring a neutral color palette with a custom pop color striped band. more

$48.00

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Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, -black/charcoal multi, Medium

Bailey of Hollywood Men's Mannesroe Braided Fedora Trilby Hat Hat, -black/charcoal multi, Medium

The Mannesroe fedora in bailey's braid collection is a bold yet stylishly sophisticated for the summers evening activities. The multi colored pattern gives this fedora an eye catching appeal and before you know it all of your friends will be asking... more

$49.99

FREE shipping

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Bailey of Hollywood Men's Waits Braided Pork Pie Hat Hat, Black, Large

Bailey of Hollywood Men's Waits Braided Pork Pie Hat Hat, Black, Large

The Bailey of Hollywood waits is a smooth and sleek braided pork pie with a traditional telescoping crown, a grosgrain ribbon hatband, and a stingy upturned brim. more

$59.99

FREE shipping

go to store
Bailey of Hollywood Men's Mannes Braided Fedora Trilby Hat Hat, brown/multi, X-Large

Bailey of Hollywood Men's Mannes Braided Fedora Trilby Hat Hat, brown/multi, X-Large

Street-wise and ready for action, the bailey of Hollywood Mannes hat is one slick straw fedora, perfect for any scene or happening. This snap-brim braided straw hat is malleable and packable for traveling convenience, and wonderfully eye-grabbing for... more

$49.99

FREE shipping

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More information about Men's Hats

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