In a year he'll be LARPing as a woman full time.

This whole "exploring your feminine side" thing is such bullshit. There's nothing "feminine" about men showing their emotions. Some of the most manly men imaginable can also be the most emotional, and not just rage and anger. But the moment you start wearing woman's clothing, that's a fetish.

And that's cool too if you keep it where it belongs, in the bedroom.

You want to wear a skirt for comfort? Kilts exist. There's no reason why we can't have manskirts cut for men's bodies (and with pockets), just as women's pants are cut for women's bodies.