Everyone is different. For me, at least during an interim period, I needed to dress more or less ultra-feminine to overcome the shame of not wanting to be male. And as I say, it is much more complicated and I struggle still and probably always will with all of this. The easiest thing is just to say that I find male genitalia as an owner to be faintly disgusting. Some of guys are literally so huge that it simply has to hurt whenever they walk or move or cross their legs. I am short and fairly petite and some of that aspect intertwines with the fear of being a sissy aspect.
Remember the Simpsons with the mini-golf challenge and the boy whose father did not win had to wear a dress in public. I don't think that I am too far off from that. It's basically the worse male fear of all, being made to wear the garments of a woman and the only thing more shameful historically was to wear a woman's clothes and to bottom.
The other thing is that I call things like I see them and certainly with the wig on, right now Jane is simply more attractive to both men and women. I very closely associate the wig with my Janey personality and as my hair comes in, I guess I will see if it is as distinguishing and attractive as the wig has been for me. That wig hasn't saved my life exactly but hair restoration takes a long, long time and thank Goddess, I had a back up.
That's one of the main reasons that I started a separate thread, so that I could deal with some of the psychological issues that might not apply to the folks "just in it for the hair" but then again some times, I still think that I am just in it for the hair. With the hair I envision, Jane, Will, it doesn't matter that much as long as my hair is blowing gently about my face....