I've been out and about in my ballet flats many times, and have walked around the block late at night in my heels, but yesterday I finally got up the nerve to go out in public in broad daylight wearing my black heels.
I didn't walk far, only about a quarter mile or so, but there were people, and I did cross two streets at a busy intersection.
This all might not seem like much to the more advanced cross dressers, but it was a major milestone for me, becoming more confident in my dressing. I enjoyed those few minutes.