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I just can't believe you could wear a flowy floral print summer dress and be considered a dependable guy by everyone. Some cultures put such an high effort to preserve their old ways that I can't see that going away in 100 years, or even 300 years. The rest of us unfortunately have to play by their rules and taboos.
Last year, my father called me up to tell me that he saw a guy wearing a dress. He was obviously looking for a "This is surely a sign of the end times" reply, but I just said "So?"
My father then asked me if I'd wear a dress. I replied "it's not for me, but I'm not going to judge someone who wants to wear one."
I can definitely see "guy wearing a dress" going from "this is horrible and the guy should be arrested for such indecency" (what might have happened 100 years ago) to "whatever" in 100 years given how attitudes changed between my father's generation (Boomer) and mine (GenX).
Oh I can see it go away in the next 100 years. Fashion can be very weird and chaotic.
Also, remember when men didn't wear pants at all?
Heck, at one point wearing tights and high heels with a big white wig was the height of men's fashion. Women, meanwhile, didn't wear high heels or tights at all because those were "men's clothing."
So even if society doesn't accept "men wearing a woman's flowery sun dress" as normal, things might change so that flowery sun dresses are seen as masculine and guys who don't wear them could be called various names.
Pants are for barbarians after all. Real, civilicedmen wear togas only. Chitons are acceptable but just barely.
Leggings and codpieces are back in fashion in 3.. 2.. 1..
My husband has wore a flowery summer dress for our daughter tea party before and it didn't make me think he was any less dependable. If anything they reason he wore it and how confidently he wore made me more attracted to him.
God damnit, Bob, how many times have I said no white after Labor Day?