Wear what you want, as long as it looks good. If you're going to dress as a woman, dress as an attractive, stylish woman, if your face and body allow it. I say dress appropriate for your location, time of day and for your body type. You don't want to look ridiculous like an over the hill hooker that doesn't own a mirror. When in doubt ask a TRUSTED friend that will be straight and tell you the truth. I ask my sister and or my ex wife, and as my ex didn't care for my dressing, I know she will be brutally honest.
Be you, but be a stylish you. What's the sense of dressing up as a woman if you're gonna look like every other dowdy woman out there that take no pride in their appearance.
Just my opinion.
