1. Tony Montana
Did anyone else embody the excess of the '80s more than the fictional Tony Montana? In his silk shirts, power-suits, and penchant for all things larger than life, the Cuban refugee turned kingpin is a standalone representative of Miami in the 1980s, and anyone who believed "The World Is Yours" was copying Scarface's style after the film was released.
Even as a broke dishboy, Tony was rocking stylish prints and bandanna headbands later copied by stylish guys like Frank Ocean. But Tony pretty much summed it all up when he said "In this country, you gotta make the money first. Then when you get the money, you get the power. Then when you get the power," that that's when you become the most stylish drug kingpin of all time.