5. Joseph Kennedy
If the Kennedy families are known for anything, it's their unfortunate luck and their impeccable manner of dress. While absolute evidence is lacking, numerous business partners and professionals have said that Joseph Kennedy was a bootlegger during Prohibition, and smuggled a huge amount of illegal alcohol into the country.
Kennedy, the father of President John F. and Senator Bobby, did successfully add to his already vast fortune with investments in the liquor business immediately post-Prohibition with contacts and networks that were mysteriously already in place. And he did it all while wearing the classic American tailored sportswear that the country's first family is known for.