Some dictators keep their fashion choices simple. 

Castro always wore his plain green military garb, and the King of Saudi Arabia wears a plain suit. But others love to go all out and show that being king means they can also be fashion Queens.

Of course, there are the kings of old, like Henry the Eighth and George the Third, whose paintings show off their feather fits and sassy attitude. But in more modern times, Muammar Gaddafi has definitely slayed the hardest. He would wear the most colorful, bold outfits, and have a great time doing it. Omar al-Bashir of Sudan, who ruled Sudan, would wear insane colorful suits and hats with graphics of his own face on them. Mussolini would actually go shirtless, and just show off the attitude. 

For these guys, ruling an entire country really seems like a shortcut to discounts on some killer fits.