1. Study your Color Season.
http://www.beauty-and-the[...]is.html
http://www.squidoo.com/pp_seasons
Your eyes, skin tone and hair will give you your color season.
Know your colors. Carry a list.
2. Know your complementary colors. Study a color wheel.
http://www.ficml.org/jemi[...]el.html Know what adding white, black and grey does to basic colors. For example, red with white = scarlet.
Match them up with paint cards in a hardware store. They are free. They show different shades of your colors. Carry them with you when you shop for clothing, jewelry, accessories and even shoes. When you know what goes together and have your matching color cards you can know instantly if that thrift shop or sale item will go with your color season/wardrobe. This will help give you a "put together" look in colors that make you look radiant.
3. Know your body type and facial shape.
They will help you pick clothing styles and wigs that make you look good.
4. If you are transitioning, at least read DRESS FOR SUCCESS to learn how to put together a work wardrobe. While dated, it is useful.
If you do these things, even if you do not pass, women will admire how good you look. You are more likely to pass a cursory examination in public than if your wardrobe screams "she has not got a clue how to dress". At the very least, you will have pride, and that goes a long way for self-confidence.
"A live lived in fear is a life half-lived." - Native American proverb.
"Inside every man is a woman who was drowned in testosterone before birth". - Wendy Jeanette Larsen
"It is better to be hated for what you are than loved for what you're not." - Andre Gide (French writer)