Leigh the importance in going out changes depending on what you are truly trying to accomplish or experience. That first time it's usually just to do it, to see if you have the nerve to do it. To satisfy in your own mind if others think you look as ridiculous as you think you probably do. You will avoid any close contact with others and be very content to just be seen from a distance and you will be in a euphoric state of mind the entire time you are out.
Then comes your second time out. You may choose one of lots of different reasons for going out. A drive wearing something a lot more risqué with the occasional getting out of your car to be seen by anyone who might notice you while still within the safety of driving away quickly. Flashing truckers on the Highway. A gay/les friendly club for a drink with dreams of interacting with others but still shying away from personal contact.
Then as you gain confidence you will want to get a little closer to others just to know in your own mind if you are "passing" or not. You really won't know the answer to that but you still want to try and find out just to build that confidence more. As has been already mentioned you will then try dressing to either blend in and not be noticed ( an I agree there is not much fun in doing that) or you will want to go out dressed as one of your own dream girls just to see what reactions you can get. I will never forget the first wolf whistle I received.
The point is it all depends on your ultimate desire. What exactly are you wanting to take place when you do go out.
You said " I have several times lately gone out with light makeup with no wig or jewelry and gone to Walmart or a drive thru and while I was a little concerned I did it" Ask yourself why you did this, why you did it that way, what were you hoping to accomplish.
I love going out and do so quite often with my wife. While with her I dress stylish but down to not attract any immediate reaction from anyone. The few time when I have gone out alone I always show more skin, cleavage, legs, and higher heels. And while I am not dressed this way to meet or hook up with anyone I do enjoy the satisfaction of being noticed for just how sexy I look (or think I look). I want to imagine myself as that woman you see from across the room who you can't take your eyes off of while remaining safely across the room.
Unlike some here and like a lot of others for me it's not about being myself. I am a male and very comfortable with that fact. It's about becoming and living the illusion I have created for a short period of time. It's an escape from reality like an actor getting wrapped up in playing a part. I enjoy it tremendously but know it's only temporary and that is what make it so important to be able to do.