Just wondered if there was anywhere in the US that a man (an “obvious” man say a tall, burly, hairy legged, mustached man or similar) could venture out in public dressed in obviously female attire, like a mini skirt with high heels and pearls, and be in danger of arrest?
Is cross dressing, in and of itself, a crime anywhere in the US?
When you say "illegal,’ you have to take into consideration how communities consider various actions. There might be a place somewhere where the police would see cross-dressing as some kind of public disturbance. Eventually it would probably be dismissed by a judge.
So go ahead and put on that dress. If they arrest you, it probably won’t stick.
No, I’m not a lawyer, yada yada. This is a message board, not a court of law, for God’s sake.
You also have to consider that there are all kinds of laws on the books that no law enforcement officer would ever bother to arrest over. Last I heard, back pockets were still illegal in South Carolina.
There is even a universal pictogram for “pedestrian crossing”. MW defines pedestrian as “commonplace,” so the sign means that crossing happens all the time. The sign depicts a man and a woman, so apparently, crossdressing by either gender is equally acceptable. 
I’m not finding anyone successfully prosecuted for cross-dressing in the US from Googling, although I do find occasional hits of teenage boys being evicted from proms and such (and reportedly “ticketed” although what the actual ticket was for was not given). In Iran it is punishable by flogging, and IIRC it is punishable by death in Qatar, but I could be mistaken on that. I recall a case where a court found it legal for a store open to the public to evict anyone crossdressing under a trespassing ordinance, but cannot find the case.
Some men need to be very careful when wearing miniskirts, especially without panties. They may be arrested for indecent exposure.
Well, there was this guy I saw walking around in the Strip District.
(I started a thread about it after I saw him. And no, I didn’t take the picture-I was talking to some other people I knew around here, and someone else had seen him. He was wearing a different hat when I saw him.)
According to this extremely hard to read college newspaper story, there was a new anti-crossdressing (and anti-pants-sagging) law enacted in one Louisiana parish in 2007.
