I often think that I changed over the wrong way, from the outside in and not the other way round. Like pretty much all of us, what I really cared about was passing, after all is it a safety issue in certain situations. Things can get ugly if you are read in some places, so I understand the concern.
So for the first six months or so when I started living full time as a woman, I wouldn't go out of the house in pants, it was dresses and skirts everyday and I always did my makeup. I was incredibly self conscious and had the same sense of being checked out and read. That folks were staring at me like I was a freak.
I was actually terrified to use the women's rest room, to the point that no matter where I was on campus I would go all the way back to the student union on the second floor where the ladies room was always empty. Only one time it didn't stay empty, and that cured me of my bathroom phobia.
After making my usual trek to the Topping building and trudging up the stairs, I'm safely ensconced in my stall and I hear someone come in. I waited a while to see if they would leave, and of course they didn't. I couldn't understand what she was doing or why she was staying so long, but I finally decided I'd just have to go out and face her.
So I flush and go out to wash my hands, and this girl says "oh good, I thought you would never come out. Can you tell me what you think of this outfit?" I noticed that she had a suitcase with her and some clothes strewn about. "Ah, ah, yeah, that looks great!" I squeaked, in my best femme voice I had at the time. I rushed to finish washing my hands to get the heck out of there.
"Oh wait!" she said, and started tearing all her clothes off. I took a quick look around and unfortunately there were no holes in floor for me to crawl into. She put on another set of clothes. "How about this one?" "Oh... Yes! That looks great too." I turned to escape, but she grabbed my arm and said "Wait, wait!" and started disrobing again.
At this point I could see that I'd be spending just way too much time as a fashion critic and decided to bail. I apologized for having to leave, but told her that I had to get to class, and she looked good in both the outfits she modeled for me. I felt bad, she looked disappointed that I wouldn't stay and help her figure out what to wear, but I was just way too nervous.
As I walked out of the student union, I decided that from now on, whenever I needed to pee, I was just going to use the nearest women's bathroom, and deal with it. Finally dawned on me then that there really was no where to run, no where to hide. I was just going to have to deal with being out in the real world with other people in a variety of situations.
It also occurred to me then that when I was really engaged with something, like trying to avoid being a fashion consultant or working on stuff, I seemed to pass easier. When I didn't think about passing is when I passed. This is when I developed my "Zen and the Art of Passing" theory, which basically is: When you don't care if you pass or not, you probably will. Actually even if you don't pass, if you at least seem comfortable in your own skin folks will act normal around you because you're acting like this is normal.
Which really helped me when next I braved using the women's locker room at the gym. I was still pretty scared, but thankfully the worse thing that happened to me is that the girl in the locker behind me stared bumming my shampoo. I have to admit, the girls locker room does smell a lot better than the guys.
It's just hard for me to look at the issue the same way now. Because I've gotten so heavy over recent years, I've given up on trying to look pretty and just started doing all my clothes shopping at military surplus. It's not so much that I wouldn't like to dress much nicer, but finding clothes that look good on me in my size has become such a chore that I just don't take the time.
Ok, maybe there is a little bit of trying to look like Starbuck in there too.
So for the last few years, I've mostly been going out in a combination of men's polo shirts, men's (well as RJ says unisex) BDU camo pants, and men's sneakers. The only article of women's clothing on me most days are my knickers.
What I expected to happen when I dressed down that much would be that I would be taken for a guy much more often, and I tried not to care about that too much. Of course, because I didn't care it never happened. I still get "Ma'am" pretty much everywhere I go. Sometimes I'll come home and look in the mirror and actually wonder how that is when I think I look so butch.
Which makes me wonder what would have happened if instead of worrying so much about what I was wearing in the beginning, I had just concentrated on dressing androgynously and letting the electrolysis and hormones do their thing. It might have made it easier for some of the folks around me get accustomed to a more gradual change instead of an abrupt shift. Maybe it would have been easier for me as well.
I think that if I was recommending a course for someone now, it would be to do it like that. Just let your hair get longer, take care of the internals and let your inner girl come out gradually.
That's my take on it anyway. I hope that this helps.
Shauna