One doesn't just magically become the Creative Ambassador-at-Large of luxury retail heavyweight Barneys for nothing. Simon Doonan has been in the fashion trenches for a very long time, and had the war wounds, and pedigree, to show for it. Doonan was interviewed by Slate on the current state of men's fashion as it relates to the male politicians currently vying to be considered as future President. Doonan posits that politicians purposefully choose to appear "unremarkable" to avoid looking vain or that care too much for their looks. He does, however, think that dictators—from Kim Jong Il to Castro—are the most stylish of world rulers. Check out the full video below here.