Bailey of Hollywood Gangster Hat

The Gangster hat 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 pearl.

Country Gentleman Bari Hat

This is one of the most luxurious Ivy Caps that we could find! The Bari is incredibly soft and comfortable. The inside is finished off with a great-looking pleated lining and Country Gentleman tip sticker.

Country Gentleman Wilton Hat

This classic turn down brim Fedora is made from GentleFelt®, one of the most comfortable 100% Wool Felt ever produced. It is so soft that it literally wraps around your head, while maintaining it's shape through almost any mishap, including rain.

Kangol Bamboo Long Pull On

Who said knit Pull Ons are only for the winter months? The extra slouchy and loose fitting Bamboo Long Pull On by Kangol is perfect for someone looking for volume, versatility, fashion, and fun either in the cooler months or in the cooler days of those warmer months. The Bamboo fabric is incredibly soft and supple, and you will love the look almost as much as the feel of this great selection.

hats.com Boris Flex Bamboo Hat

The next generation of Boris caps are here! We've designed the Boris Flex to be cooler in the warmer months, and help you get an even more comfortable fit. This flex-fit version is unlined so the air can flow through the bamboo material. It's also made with a flex-fit sweatband that stretches to fit. Other than that, it's the same great cap! This shape is extremely flattering and easy to wear. It's also a great value, since you can wear this cap however you like. Flip it backwards for one look, frontwards for another! The bamboo plant grows quickly and therefore replenishes itself easily, and makes a soft and durable material. Now we think that's smart! Go 'green' with hats.com!

Aegean Black Cotton Greek Fisherman Cap

Few images instantly capture the spirit and feeling of the open sea like the Greek Fisherman Cap. Worldwide this hat has become synonymous with man making his living from and living on the water. Aegean offers the only authentic Greek Fisherman Caps available in North America. This hat is made outside Athens and is infused with the culture that lends it a name. The cap is sturdy and rugged, yet completely comfortable and packable. The embroidered ribbon ornamentation on the bill and forward rope braid set it apart from any other hat.

Aegean Black Wool Greek Fisherman Cap

This is the authentic and forever popular Greek Fisherman's Cap! Made in Greece of a Wool blend for rugged durability during the colder months.

Aegean Cotton Fiddler Cap

The boat rises and falls in the sea's swells as a man battles to reel in a great game fish. The smell of salt is in the air with the sun glaring overhead, after hours of struggle abruptly the fish is landed. Man's history is intertwined with the sea. Fishermen are legendary and yet everywhere. The Fiddler hat from Aegean has salty sea air in its heart and wearing it will take you to the waters no matter where may be. This is an authentic Greek Fisherman Cap made in Greece. This cap is simply the timeless quintessential fisherman cap meant for a man who is his own captain.

hats.com Bradbury Cap

The Bradbury has a dapper look to it with it's delicate flannel patterns and ivy cap style. With multiple patterns and colors available, there is one sure to be perfect for you and every outfit that you wear.

Betmar French Beret

It's not your imagination, Betmar's classic wool French Beret is heavier and thicker than the usual berets you'll find out there. Simply put, Betmar's is warmer and built to last. With the vintage 'nubbie' on top and a bohemian motif, the Betmar French Beret is a standard.