I haven't had long hair in a long time. But I did have it when I taught fitness classes in a desert climate, which was very annoying. I always put it up in a pony tail, using those nice covered holders. I bought lots of cheap ones as fashion accessories. I did cut my hair very short to deal with helmet head. I had an intermediate length for awhile and could not deal with looking horrible when i would stop for lunch, etc. My hair is frizzy and wavy and cannot be tamed easily. I would look like Bozo the clown! Now I just pour a little water from my bottle over my head, run my hands through my hair and voila! I have been feeling like my hair is a little too short in the front, so I am going to grow my bangs a bit. We'll see how long that lasts.

Lisa, I always wear lipstick, too. Once in awhile when I am riding, I use clear gloss, but I like the way lipstick feels and looks. When I have gone on bike tours, I don't put make up on in the AM, just sunscreen a bit of under eye concealer for some very bad redness. Sorry, ladies, I don't feel good without it. Sometimes I wear nail polish and sometimes I don't. If I was going on a camping type tour, I definitely would not! My nails aren't long, but usually I have something on them.
As far as clothing, I have cycled in the Czech Republic, Austria, and Italy. I never felt uncomfortable in my bike shorts, but skorts make a lovely option. Yes, it's true women in other countries do themselves up more. I happen to like it. Italian women look so fashionable, even in t shirts and jeans and even if they are poor students. When my son came back from studying for half a year in Siena, he totally had changed the way he dressed. He said most European girls didn't believe he was American because he didn't wear a sweatshirt and a cap! Sorry to digress, but I say when in Rome...