2. Al Capone
Al Capone was the OG scar face, literally. He rarely let photographers snap the left side of his face, where he had three scars from a barroom brawl in his youth. During his rule of a criminal syndicate that included smuggling tons of booze during Prohibition, he wasn't just a stylish druglord; he was one of the best-dressed men in the country.
As the emperor of an incredibly profitable outfit, Capone spent a significant portion of his wealth on custom suits that helped him garner a celebrity status even as he was breaking the law everyday. With his signature expensive pinstripe suit, cigar, and fedora, Capone created the archetype of a mobster, and paved the way for the rest of kingpins to flex their steez.