Thanks for sharing your story! Interesting angle.
I’m a cis-woman that pretty much exclusively wears men’s clothes and I am still fascinated by what people use as gender indicators when I’m out and about. I get called sir from time to time despite having a 38d chest and a higher pitched voice. I don’t mind when this happens I guess, i find it kind of weirdly fascinating.
Anyway, Traditionally, women’s fashion is intentionally designed to be impractical. High heels, long nails, no pockets, restricting fits and seams that aren’t reinforced for durability. I mean: corsets anyone?
I believe when women began to become a part of the regular work force it HAD to become ok for them to start wearing men’s clothing, because they couldn’t complete their jobs dressed like that. So women were allowed that small leeway in their presentation in order to work. Lucille Ball was the first woman to wear pants on television at around this time.
Since there’s actually no good reason to incapacitate yourself with with your fashion choices other than a sense of societal obligation to be pristine and helpless (both things men have not been taught to care much about), I guess that’s why men wearing women’s clothing never took off. There’s basically no practical upside to it.