I've been growing my hair out to be more feminine, because I am not interested in the trouble or expense of wigs. I've been going to a haircutter/hairdresser for a while, and have even gone dressed, but a couple of weeks ago my wife suggested I use *her* hairdresser. When she went to get her hair cut and explained my situation to (we'll call her) Suzy, telling her I needed a cut that could be femmed up, but wouldn't look too girly in man mode.
So my wife made the appointment, and suggested I go dressed and that we go out for drinks after the appointment, since it was for 6 PM.
It couldn't not have gone better! [Suzy] was super nice, the salon is very accepting of everyone (a male stylist has a huge mohawk). She trimmed my hair, added some curl mousse, and gave me a ton of advice on what to do to glam it up, or man it down :-). She is definitely better than my old stylist.
Then we went out for a drink at a craft cocktail bar and walked around the downtown area. It was a very good day, and as always, I am hugely grateful to my wonderful wife.
I wore my new favorite skirt with little pink and blue polka dots and a dark blue top, black sandals, and gold jewelry, with a minimal amount of makeup (all that I can manage :-) ).