Well, certainly Arnold Rothstein wore bow ties.
Arnold Rothstein (January 18, 1882–November 4, 1928), nicknamed "The Brain", was a New York businessman and gambler who became a famous kingpin of the Jewish mafia. Rothstein was also widely reputed to have been behind baseball's Black Sox Scandal, in which the 1919 World Series was fixed. His notoriety inspired several fictional characters based on his life, including "Meyer Wolfsheim" in F. Scott Fitzgerald's novel The Great Gatsby ; the character who shared his name in the Broadway Musical "Legs Diamond"; and "Nathan Detroit" in the Damon Runyon story The Idyll of Miss Sarah Brown, which was made into the musical Guys and Dolls.
According to crime writer Leo Katcher, Rothstein "transformed organized crime from a thuggish activity by hoodlums into a big business, run like a corporation, with himself at the top." According toRich Cohen, Rothstein was the person who first saw in Prohibition a business opportunity, a means to enormous wealth, who "understood the truths of early century capitalism and came to dominate them". Rothstein was the Moses of the Jewish gangsters, according to Cohen, the progenitor, a rich man's son who showed the young hoodlums of the Bowery how to have style; indeed, the man who, the Sicilian-American gangster Lucky Luciano later said, "taught me how to dress."