I'm not suggesting you dress this way, I'm just letting you know that if the guy is in his mid-40s, you might be dealing with similar expectations.
How about leotard and tights with short plaid skirt and little magnifying glass on chain and trench coat and librarian heels and hair in ponytail curling into bun?
"Tell me, what is it you plan to do with your one wild and precious life?" - Mary Oliver
