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In the 60s and 70s, feminists fought for the idea that people should feel free to dress and act however they wanted and not let their gender define them.
It seems like we've taken some steps backwards since then. Men wearing dresses is more accepted now, but only in the narrow confines of being trans. I don't think Kobain or Bowie ever wanted to be defined as trans, they just wanted to be themselves and challenge cultural norms.
There's a sort of societal pressure to present as your gender when you're trans simply because it's safer and the alternative is often being misgendered and marginalized. it's also really scary to change presentation early on so early in the transition is when you'll see many sort of "overcorrect" and go overly femme or masc, but many are perfectly happy to be gender non-conforming, and many try less hard as they get more comfortable with themselves.
There's also the growing trend of femboys or guys that present more feminine, and I see guys painting their nails more than before these days.
I think a celebrity making a gesture or doing something symbolically is really cool, but at the end of the day the real signs of a cultural shift is what regular people are doing casually, and to me it feels like there's something shifting, even if it's slow going and there's pushback.
PS the trans dress thing sounds sort of accidentally transphobic, but looking at your profile I don't think that was intentional and is just an issue of phrasing.