I often go out without makeup. Of course, without makeup, there are fewer femme cues, and therefore I am probably less passable. What I do is simply not worry about it. I don't expect to be the prettiest woman in a room. If someone has a problem with how I look, they can look the other way.
If I am in a hurry, but don't want to go out with my face totally bare, I'll put on some lipstick. It makes quite a difference. And I always wear earrings. I put in a pair of silver studs in the morning and don't take them out until I go to bed at night, unless I change them for something fancier to dress up. You'd be surprised how feminizing that can be.
I have the hair issue, too. I never go out without something on my head. Any time I am out of the house, I have either a wig or a hat on my head. Usually a wig if I am going into town, even if it is just for grocery shopping. But for taking the dog for a walk, or going to the weekly fire department practise, I wear a ball cap. Although I keep my own hair short for wearing under my wig, I keep it long enough to show some curls under a hat, so the effect is quite feminine. (At the fire department, there is a brief moment when my head is exposed when I switch from my cap to my helmet - c'est la vie.)
