That would be lovely. I also like to give my sims different hairstyles for different occasions but based on same style and length. Where possible I even give them bed hair that looks a bit messy with their sleepwear. For sportswear I usually give them ponytails. And some dresses would definitely look lovely with up-dos. But I usually don't like to give my sims helmet kind of hair that covers the ears, because you can't see the earrings. I don't think I've ever seen anyone in real life wear their hair in a way that covers both ears like that. Usually, the hair is swept back behind one of the ears at least.
