Gangster Fashion

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Gangster Fashion

Part of the aura surrounding the Chicago gangster era is the music, the cars and the of course the fashion.

Diagram showing the fashion expenditures by Al Capone.

Al Capone's monogrammed light green pleated silk shirt with white and dark green pattern. See more about it HERE.

(Mario Gomes collection)

The straw boater

The straw boater was made popular by the Gandola rowers in Venice, Italy and the french Navy in France. Europe started to make a fashionable hat for all the public by making the straw boater minus the floating extended ribbons at the back. As always, once the the fashion in Europe tapers off it catches on in North America. 1899-1930's.

Al Capone (right) wearing a boater in Miami 1941. It was no longer the fashion by that time.

It became the favored hat of barbershop quartets, politicians, presidents, but mainly gangsters. These hats were only worn in spring and summer months for their cooling effect on the head.

The Fedora (stetson)

The term Fedora came from a 1882 play in which the main actress wore a soft brimmed hat. After Prince Edward of Britain started wearing one in 1924, it became very popular amongst men.

In North America it reigned from 1924 to the 1950's. It was very popular with newspaper men, detectives, politicians. Especially popular with the gangsters who kept one eye covered by the brim at all times not to be recognized by police or foes alike.

The Spectator wing tip

Invented by English cobbler John Lobb in 1868 as a cricket shoe. It was later introduced to the public in the rest of Europe. It mostly caught on with the seedy types such as gamblers, pimps and criminals. Made of colored leather and off white canvas, the public found it's appearance too gaudy for the time. In the 1920's the fad caught on in North America. Politicians, gangsters and even the president wore these shoes. They came under different styles, later being made entirely of leather and with names such as the Brogue, Wing tip or Oxfords. These are not to be confused with golf shoes whose colors are inversed and have cleats under them. They are as cool looking as ever today! I currently own 6 pairs and probably have owned two dozen in my lifetime so far.

Capone in Cuba wearing wing tip oxfords.

Spats. These were shoe covers used mainly for fall and winter to keep your ankles warm and prevent your shoe tops from getting wet and dirty. These were popular from the 1900's to about the mid 1940's.

A dead Jack McGurn wearing spats February 15,1936.


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Al Capone's monogrammed light green pleated silk shirt with white and dark green pattern. See more about it HERE. (Mario Gomes collection) The straw boater The straw boater was made popular by the Gandola rowers in Venice, Italy and the french Navy in France. Europe started to make a fashionable hat for all the public by making the straw boater minus the floating extended ribbons at the back. As always, once the the fashion in Europe tapers off it catches on in North America. 1899-1930's. Al Capone (right) wearing a boater in Miami 1941. It was no longer the fashion by that time. It became the favored hat of barbershop quartets, politicians, presidents, but mainly gangsters. These hats were only worn in spring and summer months for their cooling effect on the head. The Fedora (stetson) The term Fedora came from a 1882 play in which the main actress wore a soft brimmed hat. After Prince Edward of Britain started wearing one in 1924, it became very popular amongst men. In North America it reigned from 1924 to the 1950's. It was very popular with newspaper men, detectives, politicians. Especially popular with the gangsters who kept one eye covered by the brim at all times not to be recognized by police or foes alike. The Spectator wing tip Invented by English cobbler John Lobb in 1868 as a cricket shoe. It was later introduced to the public in the rest of Europe. It mostly caught on with the seedy types such as gamblers, pimps and criminals. Made of colored leather and off white canvas, the public found it's appearance too gaudy for the time. In the 1920's the fad caught on in North America. Politicians, gangsters and even the president wore these shoes. They came under different styles, later being made entirely of leather and with names such as the Brogue, Wing tip or Oxfords. These are not to be confused with golf shoes whose colors are inversed and have cleats under them. They are as cool looking as ever today! I currently own 6 pairs and probably have owned two dozen in my lifetime so far. Capone in Cuba wearing wing tip oxfords. Spats. These were shoe covers used mainly for fall and winter to keep your ankles warm and prevent your shoe tops from getting wet and dirty. These were popular from the 1900's to about the mid 1940's. A dead Jack McGurn wearing spats February 15,1936.