3. Fidel Castro
The cap, the beard, the fatigues—Castro has, arguably, the most identifiable signature look of any modern political leader. And while he was fading from official view due to his health problems in the 2000s, his trademark, square-brimmed olive cap—the “Castro hat”—became a staple of hipster fashion, stripped, for the most part, of its political connotations. Echoes of the Castro aesthetic can be found in the military-inspired garb worn by many reggae artists in the late ’70s.