Bailey Of Hollywood Men's Hats on Sale

+ Save this search
Showing 54 Men's Hats filtered to 1 brand and 1 discount

Extra 25% Off: FLASH18

Bailey Of Hollywood Men's Gaunt 25410
Bailey Of Hollywood Men's Gaunt 25410

This cossack style hat is made from leather and has a faux fur lining.

Get Sale Alert

Bailey Of Hollywood Men's Lord Wool Twill
Bailey Of Hollywood Men's Lord Wool Twill

The lord wool twill is a classic ivy cap silhouette in a fine wool blend wool fabric. It features a satin liner and a grosgrain sweatband. Made in Italy.

Get Sale Alert

Bailey Of Hollywood Men's Ammon
Bailey Of Hollywood Men's Ammon

The ammon is a universally wearable teardrop crown with a turndown brim it is crafted out of our elite finish body, made out of our finest wool available. It is trimmed with a Japanese grosgrain band, fully lined, with a fine woven sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Billy Fedora
Bailey Of Hollywood Men's Billy Fedora

Our best-selling Billy style is a modern trilby silhouette available in a wide array of colors. This custom woven toyo braid features a tonal braided band trim and a comfort sweatband

Get Sale Alert

Bailey Of Hollywood Men's Jackman
Bailey Of Hollywood Men's Jackman

The jackman features our low profile pinch front crown and casual brim. It's crafted out of our lightweight 4 oz lite felt that's water repellant, shape retentive, packable, complete with dust bag. Vegan leather trim and finished with a fine woven sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Lord 25203
Bailey Of Hollywood Men's Lord 25203

Our Est.1922 hat highlights heritage and distinctive styles that are classic, timeless and essential to every Bailey man of style who appreciates distinctive details with decades of quality, craftsmanship and experience. We took shapes from the archives and tweaked them for the contemporary man. Bailey satin lining with matching grograin sweatband. Made of 100% wool. Traditional fit. Made in Italy

Get Sale Alert

Bailey Of Hollywood Men's Riff
Bailey Of Hollywood Men's Riff

Our breed group salutes the pioneers of style: the experimenters, the Avant Garde, the most intriguing troubadours of style. Our most directional, stylish and sophisticated hats sit in breed. This hat is made with our famous lite felt finish, a revolutionary treatment process that takes a natural unstiffened premium wool felt hat and makes it shape retentive. Lite feltr adds a tough and indestructible element, combining style and function and is our best-selling finish. This hat is our polished version of our famous Tino hat. The polishing provides a luxurious shine and feel. A great evening look. Laser etched logo. Nail head detail on Japanese grosgrain. Comfort sweatband. Removable feather. 100 percent wool. Made in the USA.

Get Sale Alert

Bailey Of Hollywood Men's Gandy Hat
Bailey Of Hollywood Men's Gandy Hat

Gandy is a easy to wear Low Profile Pinch Front Crown with a Turn Down Brim. It is crafted out of our LiteFelt body which offers superior shape retention and water repellency. Finished with a leather and Japanese grosgrain trim and Comfort Sweatband

Get Sale Alert

Bailey Of Hollywood Men's Falc Hat
Bailey Of Hollywood Men's Falc Hat

Bailey caps are famous for their superior fit and custom patterns. The britten is a classic 8/4 cap in a work wear weight cotton blend striped fabric. It is fully lined, complete with a comfort sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Stokes Hat
Bailey Of Hollywood Men's Stokes Hat

Stokes is a classic Teardrop crown paired with a Snap Brim. It is constructed out of a light weight Winter Knit crown and Winter Braid brim and finished with a Comfort Sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Briar
Bailey Of Hollywood Men's Briar

Our poet hats embody all rugged and masculine styles that are inspired by the fortitude and courage of the old west, an ode to our western heritage. These hats are comfortable, tough, casual, functional, and rooted in masculinity. Ideal for the traveling vagabond. This hat is made with our famous lite felt finish, a revolutionary treatment process that takes a natural unstiffened premium wool felt hat and makes it water repellant and shape retentive. Litefeltr adds a tough and indestructible element, combining style and function and is our bestselling finish.

Get Sale Alert

Bailey Of Hollywood Men's Darron
Bailey Of Hollywood Men's Darron

The Darron features our Telescope Crown and stingy Snap Brim. It's crafted out of our signature shape retentive, water repellant LiteFelt body. Then trimmed with a Japanese grosgrain band and finished with a Comfort Sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Mannes
Bailey Of Hollywood Men's Mannes

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 achieving a stylish look The Mannes has a teardrop crown with a pinched front that's trimmed with a coordinating grosgrain fashion band, and the interior boasts a soft and luxurious bailey custom woven polyester sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Cordero Hat
Bailey Of Hollywood Men's Cordero Hat

Bailey caps are famous for their superior fit and custom patterns. The Cordero is our signature Contour 5 Panel Cap. It is constructed out of a wool blend speckled tweed fabric, fully lined with a Comfort Sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Ormond
Bailey Of Hollywood Men's Ormond

Our poet hats embody all rugged and masculine styles that are inspired by the fortitude and courage of the old west, an ode to our western heritage. These hats are comfortable, tough, casual, functional, and rooted in masculinity. Ideal for the traveling vagabond.

Get Sale Alert

Bailey Of Hollywood Men's Criss
Bailey Of Hollywood Men's Criss

Criss is a classic long teardrop crown with a snap brim. It is blocked out of our polished wool felt body and trimmed with a tonal Japanese grosgrain band. This hat is fully lined with a fine woven sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Lord 25202
Bailey Of Hollywood Men's Lord 25202

Our Est.1922 hat highlights heritage and distinctive styles that are classic, timeless and essential to every Bailey man of style who appreciates distinctive details with decades of quality, craftsmanship and experience. We took shapes from the archives and tweaked them for the contemporary man.

Get Sale Alert

Bailey Of Hollywood Men's Telemannes Pork Pie Fedora Hat
Bailey Of Hollywood Men's Telemannes Pork Pie Fedora Hat

The telemannes features our custom color mixed braid with a solid color contrast inset band. The trend right pork pie shape and array of colors are sure to make this style a favorite.

Get Sale Alert

Bailey Of Hollywood Men's Horton Hat
Bailey Of Hollywood Men's Horton Hat

Horton is our center crease crown paired with a stingy snap brim. It is crafted out of our polished wool felt body and trimmed with a Japanese grosgrain band with satin piping. This hat is fully lined with a comfort sweatband.

Get Sale Alert

Bailey Of Hollywood Men's boley Hat
Bailey Of Hollywood Men's boley Hat

The Boley features our Long Teardrop Crown and Casual Brim. It's crafted out of lightweight 4oz LiteFelt that's water repellant, shape retentive, and packable. This style features a leather packer strap that allows it to be rolled up and taken with you.

Get Sale Alert

Bailey Of Hollywood Men's Meren Hat
Bailey Of Hollywood Men's Meren Hat

Meren is a relaxed Low Profile Pinch Front Crown with a raw edge Turn Down Brim. It is crafted out of our shape retentive, water repellant LiteFelt body and trimmed with a western cording band. Then finished with a soft Comfort Sweatband.

Get Sale Alert

Bailey Of Hollywood Men's chesley Hat
Bailey Of Hollywood Men's chesley Hat

Chesley is our Classic Center Dent Crown paired with a Snap Brim. It's crafted out of our LiteFelt body, that is shape retentive and water repellant. Trimmed with a natural leather band, removable feather and Extended Comfort Wicking Sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Wynn
Bailey Of Hollywood Men's Wynn

The wynn features a teardrop crown paired with a unique contour snap brim. It's flattering shape is crafted out of our shape retentive, water repellant lite felt body. Then trimmed with a Japanese grosgrain band and finished with a comfort sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Waddel Hat L
Bailey Of Hollywood Men's Waddel Hat L

Bailey caps are famous for their superior fit and custom patterns. The waddell is a slim fitting contoured pub cap. It features a soft casual cotton blend herringbone exterior, and is fully lined with a comfort sweatband

Get Sale Alert

Bailey Of Hollywood Men's Barkley Hat
Bailey Of Hollywood Men's Barkley Hat

Barkley is our easy to wear low pinch front crown with a turn down brim. It is crafted out of our polished wool felt body and trimmed with a double layer, contrast color Japanese grosgrain band. This hat is fully lined with a cotton comfort sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Bryant Hat
Bailey Of Hollywood Men's Bryant Hat

Bailey caps are famous for their superior fit and custom patterns. The bryant is our signature contour 5 panel cap. It is constructed out of a micro dot suiting fabric, fully lined with a comfort sweatband.

Get Sale Alert

Bailey Of Hollywood Men's Blixen Hat
Bailey Of Hollywood Men's Blixen Hat

Blixen is our signature Center Dent Crown paired with a medium Snap Brim. Blocked out of our shape retentive, water repellant LiteFelt body and trimmed with a Japanese grosgrain band. Then accented with a removable feather and Comfort Sweatband.

Get Sale Alert

Free Shipping any 2+ items

Bailey Of Hollywood Blackburn
Bailey Of Hollywood Blackburn

Upgrade your look to the next level with this handsome Bailey of Hollywood hat! ; Classic fedora with pinched crown. ; Woven hatband. ; Brim offers fashionable protection from the sun. ; Interior sweatband for all day comfort. ; 100% paper. ; Spot clean only. ; Made in USA and imported. Measurements: ; Circumference: 23 3 4 in ; Brim: 2 3 4 in ; Product measurements were taken using size LG. Please note that measurements may vary by size.

Get Sale Alert

Free Shipping any 2+ items

Bailey Of Hollywood Riff
Bailey Of Hollywood Riff

The Riff hat from Bailey of Hollywood will gear up your look with style and intrigue! ; Wool fedora with upturned brim and center dent crown. ; Grosgrain hatband with bow and feather detail. ; Water repellant Litefelt finish. ; Interior sweatband for all day comfort. ; 100% wool. ; Spot clean only. ; Made in the USA. Measurements: ; Circumference: 23 1 2 in ; Brim: 2 in ; Product measurements were taken using size XL. Please note that measurements may vary by size.

Get Sale Alert

Free Shipping $150+

Bailey Of Hollywood Dodgson Fedora Hat
Bailey Of Hollywood Dodgson Fedora Hat

2" brim Center dent crown, laser etched Bailey logo on leather band, fine woven sweatband, designed to retain its shape Wool Professional hat clean Made in USA

Get Sale Alert

Free Shipping $150+

Bailey Of Hollywood Sperling Fedora
Bailey Of Hollywood Sperling Fedora

The classic low profile pinch front crown and turn down brim of this fedora from Bailey of Hollywood make this casual relaxed hat the perfect addition to any wardrobe. 2.5" turn down brim Low profile pinch front crown Wool Made in USA and Imported

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Jackman Caps
Bailey Of Hollywood Jackman Caps

Refine your sharp style with this fashionable Bailey of Hollywood Jackman hat! Classic fedora with pinched crown. Slim leather hatband with signature hardware accent. Short, floppy brim. Interior sweatband for all day comfort. 100% wool. Spot clean only. Imported. Measurements: Circumference: 24 in Brim: 2 1 4 in Product measurements were taken using size XL.

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Redford Caps
Bailey Of Hollywood Redford Caps

Find an ivy cap fit for any scholar of classic style with this Bailey of Hollywood hat! Classic driving cap. Signature logo hardware. Brim offers stylish protection from the sun. Interior hatband offers all-day comfort. Lined interior. 100% cotton. Spot clean only. Imported. Measurements: Circumference: 22 1 2 in Brim: 2 1 2 in Product measurements were taken using size LG.

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Boley Caps
Bailey Of Hollywood Boley Caps

Make your statement a bold one in this handsome Bailey of Hollywood Boley hat. Heathered wool fedora with pinched crown. Leather band detailing with stud and signature logo. Flat brim. Interior sweatband for added comfort. 100% wool. Spot clean only. Imported. Measurements: Circumference: 22 in Brim: 2 1 2 in Product measurements were taken using size SM.to watch some tips on how to clean your wool hats! ()

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Waddell Caps
Bailey Of Hollywood Waddell Caps

Take your look back with this handsome Bailey of Hollywood Waddell cap! Herringbone cap with six-panel construction. Curved brim. Lined interior with light bulb pattern. Interior sweatband for added comfort. 70% polyester, 30% cotton. Spot clean only. Imported. Measurements: Circumference: 22 in Brim: 2 in Product measurements were taken using size MD.to watch some tips on how to clean your fabric hats! ()

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Lando Caps
Bailey Of Hollywood Lando Caps

Keep your look pristine with the Lando fedora hat from Bailey of Hollywood! Raffia trilby fedora with pinched crown. Grosgrain hatband with bow detail. Upturned brim. Interior sweatband for all day comfort. 100% raffia. Spot clean only. Imported. Measurements: Circumference: 22 in Brim: 2 in Product measurements were taken using size LG.

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Billy Caps
Bailey Of Hollywood Billy Caps

Ugrade your look for the next season in this refined trilby hat from Bailey of Hollywood! Trilby fedora silhouette with pinched, teardrop crown. Matching hatband detail. Upturned brim. Interior sweatband for all day comfort. 55% paper, 45% polyester. Spot clean only. Imported. Measurements: Circumference: 23 1 2 in Brim: 1 1 2 in Product measurements were taken using size XL.

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Galvin Wool Twill Caps
Bailey Of Hollywood Galvin Wool Twill Caps

Find a handsome charm to complete your look with this Bailey of Hollywood Galvin Wool Twill cap. Wool-blend newsboy cap with eight-panel crown. Flat brim. Lined interior. Interior sweatband for added comfort. 65% wool, 20% polyester, 13% polyamide, 2% other fibers. Spot clean only. Imported. Measurements: Circumference: 24 in Brim: 2 in Product measurements were taken using size XL.

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Mannes Caps
Bailey Of Hollywood Mannes Caps

Stir up the pot in sheer style with the Mannes hat from Bailey of Hollywood! Trilby fedora silhouette with pinched, teardrop crown. Multi-colored knit design. Striped hatband. Upturned brim. Interior sweatband for all day comfort. 55% paper, 45% polyester. Spot clean only. Imported. Measurements: Circumference: 22 in Brim: 2 in Product measurements were taken using size LG.

Get Sale Alert

Free Ship & Free Return

Bailey Of Hollywood Graham Caps
Bailey Of Hollywood Graham Caps

Find an ivy cap fit for any scholar of classic style with this Bailey of Hollywood hat! Classic driving cap. Signature logo hardware. Brim offers stylish protection from the sun. Interior hatband offers all-day comfort. Lined interior. 65% polyester, 35% cotton. Spot clean only. Imported. Measurements: Circumference: 23 in Brim: 2 in Product measurements were taken using size LG.

Get Sale Alert
Top