@Wrongsideofhistorymyarse
The gentleman concerned appears to be wearing a padded bra.
I didn't spot that until you mentioned it but yes, you are right.
I had a boyfriend who liked to wear a sarong, kilt-type man-skirt or culottes in the summer. Smart, pinstriped gear or casual, camouflage pattern mostly. Absolutely no way that he, I or anyone else would perceive him as wearing women's clothing.
I had another boyfriend who liked to borrow my silk shirts and blouses because, he said, they felt so much nicer on his skin than rough men's shirts. I am sure that they did but I told him to stop because it was a bloody cheek.
There were other things that were a bit iffy - too many small things to be bothered to recount now - but most of all I had a gut feeling that there was something off. It was mostly about pushing people's boundaries, not just mine, to the point where they would be uncomfortable and then being gleeful about it.
What surprised me very much was that it was not him but another friend who "came out" in his late 50's and now presents as a rather hefty caricature of a cross between Dorien Green ("Birds of a Feather") and Hyacinth Bucket's sister Rose ("Keeping Up Appearances").
Maybe just a coincidence but the first step towards 24/7 cross-dressing was to very unexpectedly take a massive drop in salary in order to work on a Supermarket Checkout - and ask to be issued with a woman's uniform.
It actually makes a lot of sense, if you think about it.
I have also known men who were happy enough to dress in dowdy, frumpy women's clothes and wigs in public and who saved the glamour wear for indoor "dressing up" or time at home with friends.
We can all have very different perceptions, thoughts and feelings about the story in the Hull Daily Mail. The text and photos suggest to me that there is more to it than meets the eye. I would also be inclined to listen very attentively to anything that Tinsel had to say on the matter.