My, boomer's tomboy thread has taken quite a turn. I am fascinated with the range of behavior you've been discussing and where society draws the line between normal and weird.
I was a fairly girly girl, but I think I grew up to be a low maintenance woman. As I'm 46 and have never been married, I'm sure lots of folks wonder about my sexual preference. I figure it's none of their damn business and let them wonder. Unless I'd like to make that information their business of course...
Comfort is key. I won't wear shoes that hurt or clothes that require special attention to how I sit. I've gone thru phases of wearing skirts and earrings. Haven't worn either in several years, but I'd consider them again. Dangle earrings are kind of fun. Oh, and I have always had wash-and-wear hair. My sister has the same hair, and she blows it dry then uses hot rollers or a curling iron and then hairspray. I can't imagine doing all that.
I'm now working in an office where most of the women wear skirts, heels, hose. Even on blue-jean Fridays, they're dressed up. I'm trying not to stand out too much, but I'm sticking to flats and pants. I've been wearing sandals all summer to work, and I recently took the (HUGE) step of painting my toenails for the first time in my life. Also bought a couple of pairs of sandals that aren't brown or black!