The simple answer is that I am more comfortable in a dress, heels and full makeup. Keep in mind that I am a transgender woman and as such I was diagnosed with a condition called gender dysphoria.
What is gender dysphoria? It is a condition where you feel you were born in the wrong body. How does gender dysphoria affect me on a daily basis? Most days, I dress very casually, just like any other woman.
So, how do I go about choosing an outfit to play poker in? This is where my sense of style was inherited from my mother. She was the secretary to the superintendent of The Easton (PA) Area School District for many years.
I usually pick 3 or 4 dresses from my collection of over 400 dresses. Yes, you read that right - 400 dresses. It usually comes down to this - what colors haven't I worn lately.
Next, comes shoes. This is where it gets really fun. My wife, Sue, calls my shoe collection "The Imelda Marcos Starter Set." I own over 1500 pairs of heels. Again, you read that right - one thousand five hundred pairs of heels. They range from 3 1/2 to 8 inches. Most are either 4, 5 or 6 inch stilettos.
Makeup. I have asked this question - "Who does your makeup for you?"
For the record, I do my own makeup. My late wife, Gianna, was a professional makeup artist and taught me a lot of techniques I use today. My wife, Sue, marvels at how fast I can do mine. When Sue and I go out, I usually do hers as well.
Hair. I wear wigs 99.44% of the time. Blonde. Long. Straight. Wavy. I own over a dozen wigs currently. Sometimes for shock value, I will wear a RED wig!!!!
In summary, I feel that in order to play my best, I have to look my best. Keep this mind, what is the average male going to do when he sees a tall (I am 5 foot 11 in flats and over 6 foot 3 in heels), voluptuous (hormones and genetics conspired against me), blonde who is wearing a short dress and heels? He is going to stare. I call it using THE WEAPONS OF MALE DISTRACTION.
The late Robin Williams said it best. "You see, the good Lord gave men a brain and a penis. Unfortunately for them, only enough blood to operate 1 at a time."
I feel that in order to play my best, I have to look my best. It's like general preparing for a battle. I look at it the same way.