I'm a guy who likes to wear women's clothing sometimes. Frankly, I don't know how a woman is suppose to think anyway. I use to think being a combat infantryman, combat helicopter pilot or a combat jet pilot was exclusively man's work. Not anymore. And, being a nurse was exclusively women's work. Not anymore. I have to chuckle a lot when I see guys puffing out their chests and acting "all manly" but when their wives show up it's a lot of "yes dear." There's entirely too much "I must conform to some role" going around. I don't believe having a desire to wear women's clothing necessarily equates to being a woman or wanting to be a woman. I am totally content being who I am. I do agree there are men and women who are "wired" in a way that is contrary to the expected norms of society.
I'm happy your mother was a strong positive role model. My mother was a total bitch. She was an example of a person I strive to not emulate.