I was reading some posts here and was reminded of something from way back in my past...about 25 years ago.
There was a bar in town that advertised "no cover charge if you wear a mini skirt." Well, I've always been somewhat of a radical, so I decided to wear a mini skirt and go to the bar. I would hardly describe this as dressing up, all I did was remove my pants and put on a denim mini from my dress up stash. Everything else I wore was definitely guy.
I expected to get some flack at the door, but to my surprise they let me in, saying that if I had the courage to wear it, I was in. It wasn't a particularly busy night but I had more ladies buy me drinks that night than I have before or since. Overall it was a great time. I had planned to do it again, but shortly after that the bar closed.
I wish I had a camera to get pictures. No camera phones back then...
Does this count as going out dressed? If so, I guess I have done it! If such things were still going on around here, I'd be tempted, but somehow I doubt that a 47 year old guy in a college bar would go over quite the same way. I'd probably chicken out anyways, since I'd be too scared I'd be seen by family or co-workers.
Just today I was thinking of asking my wife to go out with me dressed up the next time we are out of town. I don't think I've ever had the courage to do this before. You gals are inspiring me so much!