Fall & Winter Hats
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Country Gentleman Wilton Wool Fedora hat
More Colors Available$64.99- Style: Fedora
- Material: 100% Wool Felt
- Brim: 2 3/4"
- Crown: Pinch Front
- Made in the USA
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Bailey of Hollywood Riff LiteFelt Wool Fedora
More Colors Available$124.99Whether you are a male or female, our Riff Wool Fedora will accentuate many styles. This Bailey of Hollywood hat features LiteFelt polished wool that is water repellant and finished with a luxurious s... -
Bailey of Hollywood Tino Crushable Fedora
More Colors Available$94.99The Bailey of Hollywood Tino Crushable Fedora's durability and style is sure to exceed your highest expectations. Not only is it stylistically versatile, but it has shape retention technology so you c...
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Bailey of Hollywood Curtis Indy Fedora
More Colors Available$94.99For a great looking silhouette, there is nothing classier than a hat made by Bailey of Hollywood. This Bailey Curtis Fedora is in the Litefelt line, which combines traditional artisanship with moder... -
Bailey of Hollywood Galvin Herringbone Ivy Cap
More Colors Available$94.99From the Est. 1922 collection, this is one of Bailey's finest ivy caps. 100% Wool 8 Panel Cap Satin lining with matching grosgrain sweatband ... -
Bailey of Hollywood Seddon Dockman Cap
More Colors Available$63.00- 50% Wool, 50% Polyester
- 2" Brim
- 8-Panel Crown
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Bailey of Hollywood Ormond Ivy Cap
More Colors Available$55.00- 50% Woool, 50% Polyester
- 2" Brim
- 5-Panel Crown
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Scala Premium Wool Felt Center Dent Fedora Hat
More Colors Available$69.99If you're looking for a high quality, premium made wool felt fedora, then you've landed in the right place! This Scala fedora is a testament to the evolution of headwear; classic and enduring with... -
Bailey of Hollywood Blixen Litefelt Fedora
More Colors Available$94.99The Bailey of Hollywood Blixen Litefelt Fedora is a timeless choice for those looking for their next favorite hat. This fedora is made of Bailey's revolutionary Litefelt wool that is both waterproof a...
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Stacy Adams Premium Wool Felt Rocker Pork Pie
More Colors Available$74.99Stacy Adams has been part of the American fashion scene since 1875, talk about tradition! Channel this classic look with this our Stacy Adams Wool Felt Rocket Pork Pie hat. This hat has a flat t... -
Stacy Adams Premium Wool Center Dent Fedora
More Colors Available$69.99A sturdy yet flexible hat, our Stacy Adams Premium Wool Center Dent Fedora holds its shape and boasts a wool felt material essential for any winter hat. Supplemented by a leather sweatband and sat... -
Stacy Adams Premium Wool Felt Homburg
More Colors Available$74.99Before "The Godfather's" Al Pacino made the homburg hat popular again, they were worn by Edward VII and most of Europe. Get your piece of the history pie by sporting our Stacy Adams Premium Wool Felt ...
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Stacy Adams Premium Wool Felt Center Dent Hat
More Colors Available$64.99Another fine hat from our Stacy Adams collection, this premium wool felt center dent fedora is a unequaled by few for its quality and price. With a feathered three pleat silk trim and a satin inne... -
Stetson Hatteras Cashmere Blend Newsboy Cap
More Colors Available$174.99The Stetson Hatteras Newsboy Cap is a blend of silk and cashmere, making it a delight for two senses: sight and touch. This cap pairs well with both casual and dressier outfits, so wear this hat for d... -
Stetson Bandera Silk and Cashmere Blend Ivy Cap
More Colors Available$174.99This Stetson Silk and Cashmere offers the comfort you need for any occasion. This cap style dates back to the early decades of the 1900s. A style that has endured such long years, just as this style h...
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Bailey of Hollywood Dalton Fabric Safari
More Colors AvailableRegular Price: $59.99
Special Price $55.00
Think up your own adventure as an excuse to take our Bailey Dalton Fabric Safari Fedora Hat out and show it off. This fedora will keep you comfortable with ventilating eyelets and a nice size brim... -
Bailey of Hollywood Lord Wool Solid Ivy Cap
More Colors Available$84.99Try out this solid color wool cap that will fit any style or mood you have to throw at it. The Bailey of Hollywood Lord Solid Ivy Cap is made in Italy with a quality wool blend. The solid color choice... -
Bailey of Hollywood Lord Herringbone Ivy Cap
More Colors Available$84.99This Ivy cap is Italian made for true authenticity. Fit the part, look great and stay warm in this great cap that comes in Black or Brown Tweed Wool. You will look great while out on the town, out for...
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Bailey of Hollywood Lord Plaid Ivy Cap
More Colors Available$75.00The of high quality fabric and great fit of the Bailey of Hollywood Lord Plaid Ivy Cap gives the wearer unbeatable lightweight comfort, as well as casual style. The wool blend tweed design is sure to ... -
Bailey of Hollywood Lord Nailhead Ivy Cap
More Colors Available$79.99You're ready for any situation, you've got you're "A" game ready. Now you just need a hat to complete the look. This classic style hat that provides Italian made comfort and durability with warmth an... -
Bailey of Hollywood Galvin Wool Solid 8 Panel Cap
More Colors Available$89.99Show your Italian finesse with the Bailey of Hollywood Galvin Solid 8 Panel Cap. This ivy cap is available in many colors to match your style, mood, or outfit. An Italian inspired style, the Galvi...
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Bailey of Hollywood Galvin Tweed 8 Panel Cap
More Colors Available$85.00Whether you're a PhD, or you just like to look smart, a tweed cap is the way to go. Tweed is a style favored by the elite of the northeast, so try it out! This Galvin Tweed hat is from the Italian Col... -
Bailey of Hollywood Brandt Lanolux
More Colors Available$124.99Do you love the finer things in life? Then the Bailey of Hollywood Lanolux Brandt is for you! Made from 100% virgin wool, this pinch-front fedora has a soft fur-felt touch. With a two-tone leather ban... -
Bailey of Hollywood Gangster Wool Felt Capone Style
More Colors Available$104.99Channel the mafia's glory days with this Capone-style felt dress hat. You'll feel like a prohibition-era lawbreaker with the hat's 2 1/2-inch snap brim, 5-inch crown, raw edge, feather accent, and wid...