I'm not referring to TV and CD events, meet-ups in hotels etc but in everday life. How often and in what situations have you observed a male wearing a skirt, dress or other quite obviously female clothing?
Here in the UK in recent years I have seen a few instances. I one case I was coming back from London one evening and walked from the Railway Station to my home. In the queue for a Club frequented by the 18-30 age group stood a couple, boy and girl of about 22 or so. Both were identically dressed. Black velvet jacket, white blouse, and a matching knee length skirt for BOTH partners, and black knee length boots. Both also had long black hair but he had a neaty trimed beard. Without making my staring too obvious I did observe him closely and it was not a "skort" or wide shorts but an identical "A" line skirt as his girfriend was wearing. The interesting thing was that nobody in the queue seemed to mind or make any adverse comment and even the bouncers on the door let them both enter the Club as I passed by. Is this a sign of greater toleration by the younger generation? One can only hope!
I was also walking through a suburb one afternoon when a teenaged boy of about 16 I'd say came out of his house to meet a female friend who had called at the door. The interesting thing was that he was wearing a girl's grey pleated skirt. At first I thought it was a rather "butch" and flat-chested girl with short hair but when I heard them speaking as I passed the voice was quite male not at all girlish. Again he was definitely wearing a skirt not grey shorts, nor a kilt of any type. Given the time of day I don't think he was going to a party in fancy dress or anything and again neither he nor the other person seemd to be concerned that they had been seen by a passer-by (me), as my being in drab at the time they had no way to know that I was sympathetic.
I have also seen a man in his 20s in a Sarong as worn by David Beckham. When he famously wore one a few years ago now, and alos admittedcthat he wears his wife Victoria's (Posh Spice) Thongs, I had hoped that this would have started a fashion amongst British men but this came to nothing, perhaps because Beckham has as many people who strongly dislike him as he has fans. What is needed is for a widely popular man, maybe a music or media star, to openly Crossdress and start a trend.
As for men wearing women's underwear, over here in the UK that is more difficult to detect as for many years now many men and boys have worn underpants which are identical to women's panties in many ways, having no fly opening in the front, elastic round the leg bands, a double gusset and being in various colours and patterns. I have however when getting changed to play Golf observed a few other players wearing Women's Sloggi Briefs as I do myself , in one case a bloke wearing a pink pair. Of course I didn't remark on this and was careful not to let him see me looking. The man in question didn't look feminine in any way and you wouldn't have gven him a second look in the street as he changed from his Golfing clothes into the jeans and polo shirt he was wearing.
Have any of you had similar observations of males in skirts, dresses, panties or other female clothing in ordinary situations, that is not at CD/TV gatherings or meet-ups?