His last name is synonymous with success in hip hop. As the son of Joesph "Rev. Run" Simmons and the nephew of founding hip hop mogul Russell Simmons, it's not hard to figure out where Diggy Simmons gets his sense of style from. Much like his 2010 mixtape, Past, Present, Future, Diggy is doing his part to carrying on the legacy of the Simmons style. Where his uncle Russell was one of the first rap figures to make it cool to rock a suit and sneakers, Diggy knows how to make that look work for himself as well.