OH I'm sorry, I always though that was being just plain Polite.
Forget skirts and heels for a minute.
You wouldn't ask a date what to expect to wear?
Showing up in jeans and t-shirt isn't going to cut it going out for a nice dinner the same way a suit and tie doesn't work for apple picking.
And to the OP -
Fully femme or just a man in a dress........
It really doesn't matter - but for F*** sake that is something you just don't spring on someone!
It doesn't matter how comfy you are wearing what your wearing.
Try and think of the other person for once!
Because it sounds like you have done this very thing before.
Maybe you wouldn't need to date so much if you showed up to the first date wearing pants once in a while.
Why is common sense not such a common thing these days.