Living in Chicago in and around the downtown, North Michigan Avenue, River East and River North areas, I have not seen any man wearing heels. I’ve been out daytime, post work hours and evening, weekdays and weekends but have not seen a man in heels. Now you do occasionally come across a CD/TV wearing heels, but that has been all. If you go to some of the clubs where CD’s go, naturally you’ll see men in heels but dressed fem. Maybe I have been in the wrong place at the wrong time, but this has been my observation.