Cyrsti, I *really* like how you look in the picture with the black hair!
With my my limited public exposure so far, I think I worry first about how my face is presenting, then the wig for sure is #2.
But after I'm out in public, there isn't too much I can do to improve my makeup, so I found myself mildly obsessed with how my hair was looking. When we were out shopping I was constantly looking at reflections of myself in windows and store mirrors to see if it needed adjusting.
It's probably a lot worse for me as I've always kept my hair very short.
Excellent points Jen! (And thanks for the compliment!) Ironically the wig colors were both very similar to my natural hair color, before the gray! On the other hand-my Mom's family was dominated by red heads.
I think becoming skilled enough to "match" my foundation makeup to my skin and then to a hair color was a very tough learning process. Plus, as I started to go public more and began to build a stable feminine persona-switching wig styles and colors was not good for the process.
Like so many other cross dressers I too went down the "blond" route, which in itself is not bad. Unless you try to go too blond like I did. The "honey blond" which I will show you in an ancient picture worked well for me for years.
I too, did the mirror thing everytime I went out. I did it for two reasons. I was trying to reassure myself that was me in the reflection and did I look the best I could. Many times I just gave up in disgust and went home-back to the drawing board.
Like you Jen, I kept my hair very short except for a brief time in the late 70's. Growing up my brother and I always were subjected to crew cuts or burr hair cuts. Even when I started college in 1968 at Muskingum and came home with hair touching my collar and ears the parents figured for sure I was a hippie.
Combined with the blessing of having no male pattern baldness in my family, I think being forced to have short hair all those years benefits me now. My hair has not had to endure a lifetime of being colored, styled, torched and permed like a genetic my age.
Finally Jen, indeed I may go back to the "darkside" this winter. I still have those wigs around which Liz and I can judge the look. One way or another, it's fun! Thanks again for the comment!