I have a question about a trickier issue: dressing as actual people/characters of another race or culture instead of as a stereotype.
For instance, an NHL player dressed as Jay-Z, part of which included darkening his skin. Now, this wasn't Al Jolsen style black face...but, yea, he darkened his skin. Apparently, he is a huge fan of Jay-Z and did it out of reverence and the costume itself clearly is not intended to mock but, is this okay?
Perhaps the answer to that is obvious (though I'm not so sure it is), what about a child who does an accurate representation of Pocahantas, without skin coloring? Or Mulan, without eye taping? I have a personal stake in figuring out the answer to this question because I am a teacher (Pre-K) and we do a costume parade at my school (personally, I'd rather avoid Halloween since we wrongly assume that everyone celebrates it (false) and that it is a non-religious American holiday (also false). As a teacher, where should I draw this line? Is Cinderella okay but Jasmine not? (I'm using the Disney princesses because of how popular they are, but I have my own issues with that for many other reasons.) Is a dread-wig as part of generic-Jamaican-guy costue wrong but dread-wig as part of Manny Ramirez costue okay?
The real Pocahontas was a 10- to 12-year-old who went around topless if not naked. You could dress your pre-K girls like that, but I wouldn't recommend it.
Any other "authentic" Pocahontas costume isn't authentic. It's stereotypical.
Other than that, here's my take on your question about dressing as actual people of another race or culture, BSK:
1) The costume would have to be very specific AND non-stereotypical. You probably could do an accurate costume for Cleopatra or Frida Kahlo, but isn't Princess Jasmine a harem-girl version of a Arabic woman? I doubt you could rehabilitate her.
2) A white kid doing Michael Jackson seems as valid as a black kid doing Elvis. But I'd suggest no face-lightening or darkening because of its historical problems. If you can't convey the person through dress alone, you probably should rethink the idea.
3) A costume such as OJ Simpson or Osama bin Laden would be hugely problematical no matter how accurate the representation. Why? Because these people are known for their behavior, not their appearance. I shudder to think of white kids acting "black" or "Muslim" to convey their beliefs and attitudes. I'd say it can't be done without veering into racist stereotyping.
If you stuck with well-known historical figures who are defined by their clothing--I'm thinking of people like Queen Elizabeth I, Napoleon Bonaparte, Abe Lincoln, or Amelia Earhart--I think you could get away with colorblind costuming. But Pocahontas, Jasmine, or Mulan? I don't think so.
In the same discussion, someone commented on a white couple who went to a party dressed as Jay-Z and Beyoncé:
Cartoon or movie characters who have distinctive costumes when worn by a child wouldn't bother me...but leave the stereotypical interpretations of our skin, hair, and other physical features out of it. It always, always, always reverts to this idea that everyone except white people has the same features and oh, aren't they just so funny, cute, hahahaha. You know, there are black people with "white" skin. So you can use our own skin and pull off your costume. Ditto for hair.
There are just so many things that you can be for Halloween. Why are so many people determined to dress up like racist a$$holes as if their lives depended on it?
Good points. Other than Michael Jackson, I'm having a hard time thinking of black celebrities who would be instantly recognizable from a costume. Maybe Stevie Wonder, Ray Charles, or Prince, but that's about it.
You want to go as Michael Jordan? Go as a generic Chicago Bulls player instead. Manny Ramirez? Go as a generic Boston Red Sox player instead.
Unless you're the world's greatest fan of Oprah, Jay-Z, Tiger Woods, Beyoncé, etc., I don't see a good reason to cross racial lines. There are literally thousands of nonracial costumes you could choose from. If you're a white person who insists on being black, I have to wonder about your motivation.
For more on Pocahontas, see Pocahontas Opera Casting Criticized and Nicole Scherzinger as Pocahontas.