I think Kurt Cobain had probably put up with a lot of shit from the macho kids for being weird, short, not sporty, weedy etc. I can totally see all these things contributing to arseholes trying to make that kid’s life a misery.
I think he wanted to throw it back at them, show defiance- I think he’d been called gay by some sporty guys, he wanted to show he was a man like them, who dated women, like them, but could wear a dress or eyeliner or hug a man unlike them, because he wasn’t hung up on homophobia, unlike them.
It’s basically “im a man, however you perceive me, however you feel i fit in or not. “ which is the opposite of what we see now.