Time to get into the deep end of the pool. I can only attest to the feeling wearing women's clothing brings to me. It's a feeling of peace and tranquility. Maybe I am different. I do not sit around and gush over makeup and nail polish. I don't know any women who do sit around and gush. I do see women who IMHO waste too much time and money perfecting claws with all sorts of decorations on their finger tips. Is that feminine? My wife does not bother with nail polish. I've never in almost fifty years seen her put nail polish on her toenails. I cannot remember the last time she wore polish on her fingernails. Her use of makeup has been limited to lip gloss. Most of the time she has no lip gloss. Perhaps males ascribe attributes to femininity based on a male mindset. Dare to ask your wife or girlfriend how she feels when she is having her period? Feminine? Or when she goes through labor pains?

What is masculinity? Dragging knuckles along the ground and bashing a woman's head with a club and dragging her back to the cave? Thinking women are no more than sexual gratification objects? Over the years/decades I've done many things and probably more than others that are ascribed to be part of a masculine role. I do not recall feeling "like a man" when I did them.

The best I can relate to the OP question is I like to believe, if I was a woman, this is what I would wear and how I would appear. It has nothing to do with feeling feminine.