I have three fedoras.
Because Inidiana Jones wears a fedora and they look cool.
Two are from Disney World and they have that Indiana Jones emblem on the side. I forgot what the other one was, I actually haven't even seen it in a long time. I should start looking for it. It looks almost exactly like the other two though.
I keep one in the car and one in my room so I am never in a position where I can't wear a fedora. I wear it at work sometimes too, when my boss tells me to put on my hat-meaning my work hat-I go to my car and get my fedora. It kind of pisses her off, especially when I bring in the whip.
I plan on getting another Indian Jones fedora from toddscostumes.com and I have a black one that I didn't mention, but it's more 30's mobster style. Oh yeah, and a grey one. What can I say, I like fedoras.