There is actually a guy in my apartment building that does. The first time i saw him, i had to look a few times to see if he was a man or woman. Once confirmed that it was a man, i didn’t judge or give him any dirty looks, because it’s how he chooses to live his life; hell; he isn’t bothering me, so why bother him. As long as he is happy, and not bothering anyone else or me, I’am as well. I see nothing wrong in living the way you choose to, if it makes you happy. Life is too short to be miserable in your own skin.
I answered this question on Quora, and wanted to share. (https://www.quora.com/What-would-be-your-thoughts-if-you-saw-a-man-wearing-womens-clothes-out-in-public-say-for-instance-shopping-or-doing-normal-daily-behavior )