8. Sidney Kelly

Sidney Kelly from Sydney, Australia. It has a nice ring to it. Between his name and his fashion sense, the man doesn’t need a cool nickname like “Babyface Nelson”.

tumblr.com

He make look bashful in his photos, but Sidney is far from it. He was notorious for “dressing well”. How dare he! Of course he was also associated with the underbelly of Sydney and was frequently in the company of prostitutes. He was arrested for assault, gun charges, drugs trading, and for starting an illegal baccarat circuit.

youtube.com