This past Sunday I was wearing my yellow jacket dress, heels and full makeup (including a new wig). I went out to a Party Store cause I was trying to finish my flapper look. I asked for directions to the items I needed twice (once from female and once from male clerks). I was able to find all the items I needed and went to check out. While moving around the store I smiled at and was smiled at by a woman customer and she was ahead of me in check out. Anyway, she was having some item price checked and I was moved ahead of her in the line. At that point I threw caution ot the wind, paid my bill and asked the clerk and customer to evaluation my 'dress as your boss' contest look, saying my boss was an older woman who dresses conservatively. The both said I nailed it. As I was leaving, the customer said to the clerk "I would not have known that was a man." Nice confirmation on my dress and presentation.
Thanks for reading. Sorry it was so long.