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Top 5 Most Notorious Gangsters in Hats

Despite causing widespread turmoil, the Prohibition era and Great Depression provided gangsters an opportunity to thrive. From bank robberies to bootlegging and illegal gambling activities, the possibilities were endless. Though criminals, many of these men dressed formally in silk pinstriped suits, bold ties, and fedora hats for men. Here are five infamous gangsters who also had a distinct sense of fashion.

Al Capone

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Born in Brooklyn to Italian immigrant parents, Capone was head of an organized crime gang by the age of 26. He was a polite, well-dressed man but was greatly feared due to his violent, erratic behavior. In 1917, he earned the nickname of “Scarface” after being slashed during a fight. He despised the moniker and always dressed impeccably in order to portray a more professional image. While Capone’s favorite gangster hat was the Fedora, he also owned several other styles that were popular in the 20s. A millionaire by the age of 30, Capone relished media attention and would often talk to reporters. His involvement in bootlegging, gambling, robbery, drugs, and prostitution, never seemed to cause him any guilt. On March 24, 1930, Capone made the cover of Time Magazine. Ironically, he was not wearing his signature gangster headwear when photographed.

George Celino Barnes

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Commonly referred to as “Machine Gun Kelley,” Barnes was born in 1895 to wealthy parents. With a career that involved bootlegging, kidnapping, and bank robbery, Barnes’ upbringing did little to sway him from a life of crime. Both he and his wife, Kathryn, terrorized banks throughout the Midwest. In 1933, Barnes and his gang kidnapped famous oil tycoon Charles Urschel. Although they did receive a ransom, George and Kathryn were later caught and sentenced to life in prison. In one of his famous mugshots, Barnes is wearing a white gangster hat known as a fedora. Although this style of men’s gangster hats is well known, it is often confused with the trilby. However, the fedora typically has a much wider brim while the trilby hat brim is short and narrow.

Clyde Barrow

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One of the most infamous criminal duos in history is Bonnie and Clyde, whose bank robbery spree spanned multiple states. The pair, along with their gang, left a bloody criminal trail that included the death of several police officers. Although their life of crime paid off for a few years, the pair’s luck would eventually run out. In 1934, Clyde hid out at the farm of gang member Henry Methvin. When a Texas Ranger discovered their hideaway, Methvin’s father attempted to turn over the pair so his son would receive amnesty. The duo died in a gun battle with police. During this shootout, Clyde wore a tan gangster fedora.

Benjamin “Bugsy” Siegel

Benjamin-Bugsy-Siegal-resizedA ruthless character known for his influence in the bootlegging and gambling industries, Siegel was born in 1906 to Jewish American parents. Like Capone, Siegel was recognized as a celebrity gangster who was greatly feared among rivals and accomplices. His popularity was attributed to his good looks and charm, which seemed to compensate some for his criminal behavior. After first specializing in bootlegging, Siegel traveled to Las Vegas to set up shop when Prohibition was overturned. Here, he operated some of the town’s first casinos and opened the door for construction of the Las Vegas Strip. During his heyday, Siegel often wore custom suits, lavish ties, and upscale shoes. While he owned several gangster style hats, such as the fedora, Siegel would occasionally sport a Panama hat too.

Charles Luciano

Often considered the father of organized crime, Charles “Lucky” Luciano was born on the island of Sicily, with his family immigrating to the U.S. when he was nine years old. Known as an ambitious young man, Luciano was the original boss of the Genovese crime family. In his earlier years, Luciano worked as a delivery boy for the Goodman Hat Company. During this time, he dreamed of other ways to make a fortune delivering goods. This led to a life of crime that included bootlegging, drug trafficking, and prostitution. Lucky’s first delivery job may have led to his appreciation of gangster hats for men. A classy dresser, he was known for his high-end smoking jackets, elegant ties, and rich collection of hats.

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