I'm not an iPOD kind of guy, but if I were, I'd have my Sennheiser 650's and one of those small portable headphone amps hooked up to it. I think it's like hi-fi. The iPOD is the source. You need good speakers as well.
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If you do get a portable amp it's worth tracking down one of the cables that goes from the dock connector to the amp input, rather than from the headphone output, so that you're bypassing the internal amp of the iPod. On one end it will have a plug that fits the dock connector on the bottom of the iPod and a stereo miniplug on the other.
I bought one from a seller called 'bassel-e' on ebay and it's a nicely made cable.
On another related topic, the Bose "on ear" headphones seem purposely designed to mate with the Ipod. Bass is full and powerful and the sound is rich. Totally transforms the Ipod. It gives you the option of not having to add an additional amp. None of the Ipods can drive any of the audiophile approved cans adequately without an external amp. The Bose OTOH is so efficient, it gets the job done admirably. Try for yourself at the Apple store. I'm sure you will be presently suprised.
All very interesting and thanks.
I already have Sennheiser HD580's and a Grado headphone amp, as well as a vintagey Headroom amp. I have Shure headphones, Etymotics headphones and Bose noise cancellation headphones.
For the iPod, my main concern is working out and long haul airplane flights.
For flights, I have just received a pair of the Sennheiser PXC-450s.
These seem to to have a higher build quality than Bose, more robust noise cancellation, and also seem to sound much better and more detailed.
Glad to know that the newer and higher storage capacity iPods have not cheapened the sound.