Why not?
Eddie Izzard does and most don't mind. If it bothers you, don't look.
I don't see why not, remember the disco era?/// guys used to wear platform shoes with chunky heels for dancing.
"When its too kinky for everybody else, its just gettin' good for me."
(Kinky Freedman)
As long as they can walk in them well, yes.
I like a man in cowboy boots & jeans, but high heels, NO.
A low heel on boots or certain shoes is fine on a guy - as long as it still looks masculine and not too fussy.
It's a different story if it's a CD or transgender person though - the skies the limit as far as heels and shoes go.