1. Johnny Cash
If you thought Kanye West, Jay-Z, and A$AP Rocky were the first ones to dress all murdered out, then allow us to introduce you to the guy who was simply known as The Man in Black. Johnny Cash rocked all-black everything in mourning for the perpetually downtrodden people he came across in his travels, and looked damn good doing it.
This champion of the people transcended country music to become known as one of the most influential musicians of his time. His romantic outlaw image essentially founded the notion that any desperado cool guy could express his bandit and anti-establishment mentality in all black garb.