Re: hair. I just finished 6 rounds of carbo/taxol. Shortly after the first round, I told the hairdresser to cut my hair short, indicating about an inch, and to do whatever style she wanted. She seemed to have a very good time cutting it, and gave me a cute short haircut, but most of it ended up significantly longer than I had indicated. When it was falling out ~3-6 weeks later, it still made a mess all over my house (although most of it ended up in the new hair catcher that I had put over the shower drain). If I were doing it again, I would just shave it off beforehand to avoid the cleanup.

I agree with cancerback that having a wig fitting and trying before buying would be best, if that's an option. But I did buy two wigs over the internet, and I have been wearing one of them.
I felt like wearing scarves and hats in public would scream "chemo!" and would make me self-conscious. First I bought an $80 wig with short sandy blond hair ( my partner was lobbying for something other than the normal ~80% grey/ 20% mouse brown). I didn't really like the way it looked (I thought it looked like a wig and sort of stuck up of my head), and the color made me self-conscious. It fit fine and was comfortable enough. Then I bought a ~$300 wig in about the same style, but a very close approximation to my natural hair color, and which could be parted in the front (but not along the top). I felt this one looked like a wig in about the same way as the other one. This one feels quite snug, but it stays on fine. I wear the grey one most of the time when I go out of the house, and I don't feel self-conscious while wearing it. I don't think it's super-obvious that it's a wig to people who don't know me. I have worn it all day a few times, but I'm not working, so most days I only wear it for 1-3 hours. It's comfortable enough. I wear a "chemo cap" at home the rest of the time.