Oh, go for it! I'm a woman, and I've dressed as a few male characters, such as Zorro, the Blue M&M, an Old Man, St. Michael the Archangel, and a priest. My brother likes to dress up a lot as Jimi Hendrix, too.
The standard outfit would include an Afro (or Afro wig), a hairband, a moustache, a psychedelic shirt, a vest, and a guitar. (You could buy a toy guitar, or make one out of cardboard or plaster.) As an African-American, I wouldn't mind if you made your skin a little darker with make-up; just don't overdo it and look like you're in blackface. Look at these!
Https://www.google.com/search?q=jimi+hen... http://www.messynessychic.com/2014/01/22... http://www.costumesupercenter.com/mens+c...
I cant really gove you an answer,but what I can give you is a way to a solution, that is you have to find the anglde that you relate to or peaks your interest. A good paper is one that people get drawn into because it reaches them ln some way.As for me WW11 to me, I think of the holocaust and the effect it had on the survivors, their families and those who stood by and did nothing until it was too late.