I can't recall ever receiving a "strange" comment, but I'm often asked why I'm in heels.
I guess because I'm tall, it's expected that I should only wear flats.
I do tend to get a visceral facial response from some women when I'm "dressed up." I call it the snarl.
And I'm using the term "dressed up" loosely. If I wear something along the likes of a sweater dress with heeled boots, I get the once-over followed with a snarl. It used to bother me, but now I get amusement out of it.