While checking out Foreign Policy magazine online, (yes I am a well-rounded reader!), I was surprised to come across this article The Devil Wears Taupe. An amazing tongue in cheek article about personal style of the world's dictators. Although it is partially to poke fun, it seems like a great illustration of how one's personal style can come across to others.
Most of the guys are pretty consistent in their look. Outside of the miltary fashions, I don't know if any of these looks really scream, "I am a dictator". Well, except for Mugabe's modern Hitleresque mustache; it may not be trend setting but it is innovative.
My top pick for the strongest style personality is Omar Qadaffi with Kim Jong Il as a strong second. I don't think anyone can fully duplicate the looks of either of these guys. They own their swag!