A Culture Of Clones
I'm not sure about drag queens/cross dressers. On the one hand it may signify breaking gender norms by dressing in the opposite gender's clothes but on the other that precisely seems to reinforce the said gender norms imo. Male to female cross dressers mostly dress in the most attention seeking outrageous clothes while female to male cross dressers dress in the typical drab male garb. It seems in this society it's more acceptable to dress as a woman than to dress in anything out of the ordinary as a man.
Really? Hard? You're still as pleasant You with that avatar seem to embody everything I find wrong with menswear. Keep to the task of dictating everyone how they should wear the tight range of outfits you've worn all your life and most likely ever will.
Good for you. It's like arguing against the burka with the fundamentalist patriarchs. It's a hopeless case but somebody has to do it.
I definitely think people on SF can be a little too conservative and hermetically sealed to certain sartorial concepts.
But I honestly don't get the tone of the initial gifs / memes... No one is stopping men from wearing something 'not black tie' to a red carpet event?
For example they could buy a Tom Ford or Gucci whatever tuxedo with birds of paradise printed silk fabric as the main fabric, so the choices and variety are there. I've even seen completely sequined Tom Ford (I think) tuxedos which would still be in the spirit of black tie.
But most people aren't fashionable truth be told, and don't want to stand out in anyway, even if its for positive attention. I was quite shocked when my tailor told me that, but he's right. Most guys, even those into expensive bespoke, don't want to turn heads - they want to 'get the rules right'. Some even want to completely blend in.
By the way, you referenced Prince William. Again, another person who would probably be the first person to tell you he is not interested in fashion or even style. His dad would have worn some much more funky 'dandified' outfits on the same trip, without doubt, but again, everyone is different.
The question you are posing for discussion (if you are being serious, I can't tell) is more a question of human nature, not society's rules on what men must wear. There's plenty of freedom in the West to wear whatever you want, but you have to be confident and bold enough to be looked at and judged as a failure or success in the expression of what you wear.