Love my ipod, Hate my ear buds....

I have a pair of Shure Se420 which I then upgraded to the Shure SE520. I like them both, although if I had to do it over again I would have gone straight to the SE520, they are just that much better.

My favorites have been Westone UM2's (with the Shure "black foamie" tips). The Westone family sound seems to be head and shoulders more natural and refined than the earphones of other companies, IMHO.

Now the Westone 3 has just been released in the past couple of weeks. WOW.

I've got a pair of Westone 3's at home and they are just a bit more neutral top to bottom, more extended in the treble while still refined, and more detailed in the bass while still very deep in bass.

Overall it seems a very noticeable incremental improvement top to bottom, while retaining the very natural and musical family sound.

I've tried almost everything out there and I think that for the audiophile who is sensitive to natural and refined sound, the Westone 3 or UM2 are best.

Also Westone seems to make the most comfortable in-ear earphones, which is a MAJOR issue for many people with these types of phones.

Art

try the denon c-751 for around $100.00 the sound is very nice.

I was in your exact situation about 6 months ago. Couldn't keep those damn stock Apple 'phones in my ears more than 5 minutes before the pain outweighed the music, which itself added to the pain as the sound quality was awful (goes without saying). After doing a little research the Sennheiser CX500 seemed to get good reviews, and after finding them online at B&H Photo for 60 bucks I took the plunge. I haven't compared them to anything else, but I can keep these things in my ears for hours with no discomfort and the sound is nicely balanced and refined. A huge step up from the stock iPod headphones in every way. They also have a neat little slider volume control on the cord that sometimes comes in handy when it's not convenient to grab the iPod and work the wheel.

Best of luck.

Another vote of support for Etymotic Research. They sound great and are very comfortable for people with any sized ears. Cheers,
Spencer