I enjoy expressing myself through what I wear. I usually wear things that reflects the music I like, since music is probably what I'm most passionate about in life. So I usually dress like women did in times where folk music was most popular. I.e., late 50s, 60s, renaissance-esque. I like loose,flowy, retro clothes. Some of my friends think I dress like a hippy, haha. When I can get away with it, I don't wear a bra. At least once a week I'll go braless, and in the summer even more. I've had this hippyish/folksy/boho style ever since probably mid-high school, but it's always been with me. The only time I didn't really dress in this way was middle school and early high school, where I was a wannabe skater/punk girl. That was hilarious.
I also love history (which somewhat coincides with my love of folksy-type clothing). So every once in a while I'll dress somewhat similar to certain time-periods that interest me a lot (rennaissance, medieval, 1700s, 1920-70s, etc).
Other times, though I don't give a shit and will dress like a hobo, not brush my hair, not wear any make up. I usually keep my make up as minimal as possible, but I like to look nice.
Here's a blurry pic of me in one of my favorite dresses I ever tried on (though I didn't get to buy it) :(