The first time I flew dressed i did it on a flight from home to someplace else. I did that so that IF I ran into problems, i would have the option of running back out to my car and changing. It just helps your piece of mind to know you have a back up and punt plan available.
A few things to keep in mind.
- Shoes - they have to come off going through security. Remember your going to be standing in a line of people when you have to take them off, so you might not want to be messing about with little tiny buckles. You CAN if you want to (I have) but you need to be mentally prepared to be hopping about on one foot while you mess with the straps! lol
- Sweaters - If the sweater is large and bulky, and clearly not the only top you are wearing, they MAY ask you to remove it. That could be fun while wearing a wig.
- Corsets - don't do it if they have a large metal content like the clasps or boning. You do NOT want the metal detector going off. It wouldn't be the end of the world, but the added attention is likely to make you a nervous wreck and is a hassle you would be better off with out.
- Jewelry - Like I said with the corset above, don't wear it through security. Chuck it in your carry on and put it on after you get through security.
Most larger airports (not all) have "Family" or "special needs" restrooms. Austin and Atlanta do, but I have been to some that don't (DFW). In that case, that's the one you want to use. It may be that the airports where I didn't see this type of bathroom might have had one, just not along side every other set of bathrooms. If these are not an option, you need to ask yourself an honest question - do you pass well enough for people to now be sure if your male of female? Don't answer that here - too personal, but YOU need to answer that question for yourself and then do what you think is best. As you have already indicated that you are probably not going to wear make up. . .