Have you checked menswear shops, like Men's Wearhouse, or tailor shops where you get custom fit suits? I'm pretty sure the ones around here stock a few fedoras, along with top hats and even a few bowlers.
I just recently got a nice khaki suede one at an antique mall, for $7. It's a pretty big upgrade from the cheap one I got at Target. I was talking to a guy at the flea market who deals in hats and he said that if you can find a vintage one for less than $50 it's a great deal, because they're popular right now. He sells a variety of fedoras, ranging from $25 on up. Some are vintage, some are newer, and he has a pretty good selection. Another place that I've seen something you might like are at Bass Pro Shops. They have one that is kind of similar to an Indy hat, but I'm not sure of the pricing.