I went on a big mountain bike ride with 5 guys last year. It was a full week of riding in the dirt with these guys. No showers. No mirrors. Oh but I did have a little mirror. I tried to keep myself tidy. I gave up on the 2nd day. I just kept my hair tide back and my face clean. But you know what? It did not matter what I looked like to the guys at all. As a matter of fact my husband likes a girl who is not fussy with her looks. He cares more that I am happy and having a good time.. i will say cutting your hair shorter might help but short hair can be funny looking too after riding a bunch of miles. Maybe just cutting shorter but still be able to tie it back would be the way to go. And as far as the nail thing goes I trimmed all my nails including toes so i would not have to think about it. And my nails grow like crazy.