But the parent comment did provide further context:
> Fashion is very much about who is wearing it, why, and how.
So wearing a dress is fine if the person wearing it is willing to concede at every moment that they're being socially deviant. The moment that you just wear a dress and make no attempt to justify yourself in terms of larger culture is when things get bad. Wearing a dress and acting like it's no big deal is an affront to the logic of someone who knows for a fact what you're doing is deviant..and they're convinced that you deep down know it too. You're more or less saying they think wrong in a very fundamental way. That gets people very upset.
If you saw a guy in otherwise ordinary circumstances wearing a dress and didn't think it was unusual, well, you lack situational awareness.
There's also the utilikilt...
Try walking around as a man in a dress in 95% of the US.