I last wore a tie three or four years ago when I had lunch at The Ritz. It was obligatory. Men must wear coat and ties. No exceptions. I bought a tie for the occasion. The lunch was worth it. Before that it would have been decades since I wore a tie. I don’t remember any specific occasion. I still own my Ritz tie - it’s at the bottom of my sock drawer, still knotted.
I wear shorts only when I’m cycling or to the gym and even then I prefer standard or ¾ length shorts, never short shorts. If I was ever to try a skirt, it would have to be along those same lines - a knee length pencil skirt or midi. I admit it’s tempting for the experience sake.
As to feminisation, the femininity of my boots is certainly part of the appeal. Cowboy boots with heels (or without for that matter) do not appeal to me. I very much like the feminine styling of my boots. Whether it’s because it adds a touch of the forbidden, or is provocative, or I like the idea of stepping out of myself - I’m not really sure. Probably a mix of all these things and more. But it’s there. I like their femininity.