There are at least two senses of the expression "feel like a woman". The first, as so many have said, relates to emotions and attitudes - i.e. to know how a woman feels about things, her sentiments, her reasoning, her emotions, etc. I doubt whether a man can experience that, regardless of clothing.
The sense in which I want to feel like a woman is of a more physical kind - and, for me, is mainly related to the clothing. What I mean is tht I can, to some degree, experience the sensations that a woman experiences when wearing female clothing. I know what it is like to have a bra round my chest and its straps over my shoulders; I know how nylon stockings feel as I walk; I know the different feelings that come from a tight skirt and from a flared one; I know what a girdle feels like on my tummy and my bottom; I know the feelings of unsteadiness in high heels; I know the feeling of airiness in a light dress on a breezy day..... To that extent I think I have some idea of what it feels like physically for a woman wearing those clothes. Even then, I accept that my different shape, my different anatomy and other factors mean that the feelings are not exactly the same.
