I tend to see it the same as blackface.
I am not generally against white people painting their faces to appear black, and not generally against men disguising as women, but it is often done in a way that reinforces oppression.
And I am sure you can use the disguise to highlight that, for example, a man in a dress behaves the way a woman naturally would if she didn't have femininity imposed on her.
But I am very sceptical of the whole thing, and would never declare all of it harmless.
Many women say that, to see whether women should be doing something (for example putting on makeup) one should ask whether a man doing the same would look ridiculous - and if yes, then it is ridiculous on a woman, too.
But I think if that's what you want to show by putting men in drag, you have to explicitly say so. Otherwise the message will be lost.