Some might think I'm crazy, but even with hair I want to be able to wear a hat. Is that a problem? I play baseball/softball some, so I would want to use a hat then. Also, bike rides or something like that I would wear a hat or helmet. Will this be a problem?

Also, what about winter caps?

Hats aren't a problem. Friction is the real enemy and a hat just kind of sits there

yes dont worry about wearing some hats. They wont get destroyed just because you wear a cap.
I wear sometime caps (mainly because if i dont want to care about my hairline on this day) and nothing happens. The only problem is, that if you take your cap off it could look a bit wiggy, because of course you cant style it beneath your cap.

I had to ware a hat for one month because BA f*ck me over. It was either a hat or a crappy unit. It was ok for hats at work so I was lucky. I figure someone would ask why the hat all of a sudden but they never did... IMO, with my style, once that hat is one, it stays on. Wig hat hair is ugly.

Once you wear a hat it flattens the hairline and looks wiggy and makes the hair look dryish.. at least thats my experience. It means not wearing a toque in the cold winters going to work but able to wear one going home. Around the head ear muffs do the trick

it sucks when you have to wear a wool winter hat outside in the cold it sticks to the glue