I think short tight skirts and pointy stilettos are as impractical and ridiculous on men as they are on women. I've never worn either, and never will. His specific choices suggests he's oblivious to the harms of misogyny, and male gaze, and the sexualisation of women's lives.
He's right though, with the exception of underwear, there's no intrinsic reason for clothing to be gendered. But then I'm a Scot, and men wearing skirts is normal here - as in many countries around the world.