Bose is not an issue of bang for the buck. People assume you get quality for money. That is not the case with Bose. I've listened to and own a few good headphones and Bose would still be a bad proposition at $19.99. Bose headphones do not sound good.
Anyhow, you can get good sound from an iPod. It depends a lot on if you're using a lossless codec and the quality of the original recording. If you're listening to a lossless version of a quality recording, you can get great sound.
As for a recommendation, you'd probably like the Grado lineup. The SR-60 (about $65) is one of the best entries to good sound. If you want to spend more, there's also a SR-80, SR-125 and a SR-225 in your price range. Grado also manufactures the Alessandro MS-1, which has a cult following here.
I'd go with the SR-60 first. It's the cheapest and is likely to curl your toes. It's amazing, especially for the price. Be careful, it might turn you into one of those audiophiles you don't want to be!