1. Dress your age. If you aren’t a junior, don’t buy your clothing in the juniors department
2. Dress appropriately for the situation. A cocktail dress at the mall isn’t optimum. Make up needs to be appropriate.
3. Crossdressing is an illusion. A genetic woman can go out without any make up and can look a mess but not look like a man. You can do the same as a man and not look like a woman. You need to constantly preserve the illusion and this involves diverting attention away from your flaws and using clothing and most importantly accessories to preserve the illusion. I do not need glasses but found they feminize me so I bought some (in the women’s section of an eyeglass store). wearing men’s glasses simply is not good enough in 99% of the people I know. I wear a hair band, diamond engagement ring, chain bracelet, necklace, earrings that dangle, and red lipstick because many people have critiqued me and said these things feminize me. The red lipstick and nail polish divert the eyes away from other parts of me.
4. Choose a wig wisely, This may be among the most important things you do. Length, color, style all matter. (If it is too perfect, it will look fake.)
5. Hair removal is always an issue. You think nothing of spending a great deal of money on clothing and cosmetics so spend some on a quality razor. Consider hair removal on your face if necessary. I had laser hair removal and it was the best thing I ever did. Use the right foundation to cover the beard but shave it off first! covering is not as good as removing. Shave closely and several times.
6. Apply make up skillfully.
7. Cover your arms if you need to. My arms are larger than a woman’s so I wear some type of top. This means I never get to wear sexy cocktail gowns and expect to pass but I can usually find something nice with sleeves. Cover your Navy tatoo!
8. Keep your skirt length appropriate. In fact, keep everything appropriate. Anything that looks out of the ordinary will be noticed and once you are noticed you will not pass. Much of the time if others really noticed me i would not pass yet somehow I pass extremely well. Why? Because I blend in and fly under their radar.
9. Avoid direct confrontation with anyone and when it i necessary to interface with a waiter, store clerk, etc. be prepared. When i go to the grocery store i know they will inevitably ask me paper or plastic so I am ready and reach for a plastic bag. I know I will be asked cash or credit so I have my cash or credit card in my hand where they can see it before they ask. But if I have to speak, I speak softly and quietly and smile.In a restaurant, point to the menu item as you order. This reduces the need to fully speak in detail.
10. Choose where you go in public carefully to minimize problems. If you don’t really pass, stay out of the ladies’ room. I go out at any time of the day or night in Times Square and pass but I avoid groups of teenagers like the plague. They will notice and if they notice they will not notice quietly.
11. Walk like a woman not a caveman.
12. Relax. If you are afraid, you will walk like you are afraid. Have confidence.
13. Carry a mirror and use it. Men don’t need much attention but women need constant attention. Walking from the parking lot to the Mall can result in blown hair. Eating can alter make up. Be prepared
14. Smell like a woman.
15. Be self aware. Know your limitations. Unless you have practiced dancing like a girl you probably won’t do it like a girl.