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Image from Mohammad Nadir on Unsplash. |
During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.
Soon I called the cross dressing I was doing, dressing for
success. Mainly because I felt better as I did it. The sad part was, very soon
the feelings of gender euphoria went away, and I was back in my unwanted male
world where I was expected to succeed. During that time in my life, I was able
to barely keep my head above water and still slowly improve my feminine basics
in such things as the makeup arts. I guess all those hours of watching my mom
apply her “face” as she called it, came back to help me. This was the 1950’s when
women took their appearance much more seriously than today. All women were
expected to dress for success.
As I barely stayed afloat with my cross-dressing challenges,
it soon became more evident to me that there was much more going on with me than
met the eye in the mirror as I tried to appreciate myself. It was about that
time, when the internet showed up, and I was able to research terms such as gender
dysphoria and transgender. Suddenly, I discovered who I might be and certainly
found I was not all alone. It all started to make sense why my urge to cross
dress never really seemed to go away. It was always with me in the back of my
mind.
Soon, as I joined the world as a novice transgender woman,
dressing for success largely depended on if I could go out into the world and
blend in. I began the easy way by trying my hand with shopping mall clerks who
for the most part were only nice to me for the money I needed to spend so I
could be more fashionable and feminine. From there, I branched out to challenge
myself by stopping to eat lunch and face servers one on one to see how I did. I
did well, and very rarely did I have to run home and wonder what I did wrong
and go back to my gender drawing board. I did not realize it but what I was
doing was replacing my mirror time with time in front of the public. A very
valuable learning experience as I discovered venues such as coffee shops, bookstores
and even antique malls where I could shop and relax.
Each experience helped me to learn more about myself as a transfeminine
person and then dress for success from it. To quit being so flamboyant with my
wardrobe and wigs became my new goal as I was settling into my new life. People
began to know me quicker, so I needed to be better in my approach to dressing
for success. I learned I did not have to lose any of the enjoyment I
experienced as a trans woman; I just needed to follow the lead of the cisgender
women around me. I did not necessarily have to dress down for the grocery store
and up when I mixed with the professional women out for a drink, but it helped
me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.
At times I even took my dressing for success to the extremes
to be able to judge what the public was thinking of me. I used to wear my best
sunglasses so that strangers could not see my eyes and tell I was looking at
them, but were they looking at me? And one of my favorite “props” to use when I
went out to be alone was my cell phone which I always had handy when I turned
out to be the only woman at the bar. That way, I was trying to show anyone else
I had someone else on the way, and I was saving their seat.
To be sure, dressing for success as a transgender woman was
always a more complex process than doing it as a man. From undergarments to accessories
such as jewelry, wigs and purses, women naturally lead a more layered life
which can be reflected in the way they dress. I certainly had many more
compliments on my outfits as a woman than I ever did as a man. Primarily, it
was because it was something men never do and often, many cisgender women used
compliments as simple conversation starters when they were curious about me.
As with all cisgender women, dressing for success is something
transgender women must learn. The problem being we come from such a vastly
different background to do it. Almost none of trans women had the benefit of peer
pressure and a mom to guide us through the initial makeup process. Our
workbooks were blank when we started our gender journeys. Playing catchup was
not a fun game to play for me as I found making up my face was different than
painting model cars. Most certainly, dressing for success was a lifelong
experience for me.