The most powerful and most profitable druglord of all-time kept it breezy in his native Medellín, Colombia. As a hero to the people, Pablo never appeared in too much flashy garb, opting instead for lightweight suiting and short-sleeved shirts that were ideal for the heat of his home country. He was considered a "Robin Hood" type figure who gave significant funding to the construction of hospitals, schools, churches, and housing in impoverished areas, and so Escobar dressed as a people's champion outfitted in plain and stylish clothing. But his simple and classic wardrobe didn't deter him from setting up one of the most complex and deadly cocaine smuggling networks of all time.