gangster

Dry Eye from The Gentlemen

In Guy Ritchie’s The Gentlemen, Dry Eye (played by Henry Golding) is a gangster who works for Lord George, though he soon deviates from his boss’ plans in order to secure his own fortune and place in the world.  Dry Eye makes an offer to Mickey Pearson for his cannabis business in order to drive the price down for another man, but this soon proves to be a mistake.  Dry Eye’s most striking clothing choice are his leopard print loafers that he wears when confronting Mickey’s wife Rosalind toward the end of the film.

Mickey Pearson from The Gentlemen

Mickey Pearson (played by Matthew McConaughey) is the main protagonist of The Gentlemen.  Mickey has risen from poverty in his home country of the U.S. to become an exorbitantly wealthy cannabis farmer and dealer in the UK.  Mickey decides to sell his business in a bid to retire, which runs him afoul of several prominent characters including Dry Eye and his associates.  Mickey’s clothing is often a little eccentric or over-the-top in either color or print, making him a fun character to emulate.

Thomas Shelby from Peaky Blinders

Thomas Shelby from Peaky Blinders

In Peaky Blinders, Thomas “Tommy” Shelby (Cillian Murphy) is the leader of a gang in 1920s Birmingham England. After he returned from World War I, where he was a decorated Sergeant Major, Tommy was disillusioned with war and determined to move the Shelby Family up in the world whatever it took.

John Dillinger

John Dillinger

John Dillinger (Johnny Depp) was a notorious and charismatic gangster during the Great Depression. The film, Public Enemies, chronicles his final years as he’s pursued by the FBI.

Steelbeak

Steelbeak from Darkwing Duck

Steelbeak is the chief agent of F.O.W.L. (Fiendish Organization for World Larceny). He is second-in-command and team leader of F.O.W.L. He is one of Darkwing Duck’s nemesis. He is a suave and urbane rooster who acts like a 1920s gangster.

“Scarface” Tony Montana

In Scarface, Tony Montana (Al Pacino) is a Cuban refugee who arrives in Miami with nothing in his pockets. Through determination and a strong dose of violence, he rises to become a powerful drug kingpin. Don’t forget to accessorize with Tony’s “little friend”.