Wow- this is so great!
She sounds like she is well ahead of you and you might want to ask her to talk to you about what she sees, what she thinks you feel, what she feels, etc and keep it very trusting and just stop if it gets hard- since that means that some nerve is being touched, so needs special care and going back a few steps.
I think the answer re makeup is that she sees it as a way to create a look and the understanding is that it is a banner message- and she thinks, obviously that it is just fine to have it be neck up only- since that is how she thinks about it.
There is theoretically no difference in legitimacy between makeup and wig in terms of being a surface application to create a new surface appearance, but her feelings are a great example of how we humans process our messaging.
Go with the boy cut fashion statement now and let your hair grow!
I know for myself the biggest thing is accepting myself as a woman, and not feeling like my appearance is needed to prove it. I think that females who are secure, like your wife, wouldn't feel less of a woman in tshirt and unshaven- just that they haven't dressed up and made themselves femininely attractive in those dimensions yet. She has fully extended that safety to you.
I have found that when I am feeling I am a woman in emotional state then I want to be dressed in certain ways, but when I am not, I try to think of my sisters who are dressed in plain unfeminine clothes, and find a little comfort in just realizing that it isn't my preference, but soon enough I will be able to enjoy my dresses. Most women today do not get to look their desired best most of the time- which is not great, but I imagine if I complained to one, she would say, well- welcome to the woman's world!
