I should have given you a little context Emma, because you don't really know much about me. I wear women clothes all the time, and usually wear some make-up even if it's only lipstick and a little powder.
But I don't really try to "pass" and if anyone is paying close attention they will know I'm not a woman. But I don't accept the idea that it is necessary to be a woman for me to wear dresses, get my nails done, or wear make-up. I think this is a very important point because it shifts the question from "how can I look like a woman" to "how can I look pretty", without the seeming requirement for pretty and woman to be synonomous.
And it makes it easier for those who are giving you fashion advice. Because it is a much easier task to have a man look nice wearing a dress than it is to have a dress disguise the man as a woman. I have a friend that I go shopping with who has a good eye for what looks nice on me, and she doesn't try to disguise the fact I'm a guy. She will say things like "your shoulders are too broad for that top", and "you have too many muscles for that", and she would say, if she wasn't so polite "you don't have any cleavage so you can't wear that."
So I would say that the first thing you should decide is what you want to accomplish, do you want to look like a woman or do you just want to wear pretty things and look good in them. Each of us has our own answer for that.
My goal is to be able to look good in pretty things, and to have a girlfriend with whom I can go shopping, share clothes, get our nails done, and...... other stuff
But if you do go for a make-over I would really suggest that you do it wearing the clothes to go with it. There are guys who wear make-up and get their nails done in total male-mode, I guess they are not CDers at all but just want to look good. And if that's your plan then it's best to wear guy clothes. But if you want to look pretty in a particular dress, then you really should be wearing that dress when you get the make-over, so that the shades and colors of the make-up they choose matches what you're wearing. Like it would be totally inappropriate to have really glamorous hair and make-up if you're only wearing an old jean skirt and casual tunic, for example.
And if you don't want to go to Macy's in the mall where everyone can see you, there are salons that will give you a make-over and often you can arrange for it to be done in private. They will charge you for it unless you buy a lot of their product. Last time I did that I spent $250 there, and loved it so much I went back and bought my daughter a gift certificate for it.