Since wearing pantyhose is way too usual nowadays and does not change the “street view” too much unless the pantyhose are way too unusual (pun intended), wearing a mini skirt and high heels is a definite step further.
If you ask me, I think the guy looks OK, I like the style. Most important, he looks neither like a transvestite nor like a woman. Actually, nor like a guy in women’s clothes.
You know what? That would not change the “street view” either ;-)
Thanks to porter.