Given the rarity of seeing someone present as a man but wearing heels, I would probably fit into the 2nd and 3rd groups there. In that position, I would wear a skirt in public way before heels though. Hats off to those that choose em, but for anything longer than a twirl around the room, they look agonizing. So like 30s to a minute I guess it would just be uncomfortable, but after that I feel like my feet would implode and need therapy to work again.