Headphones for iPod.

Check out the Etymotic ER-6i (the i is for iPod) at the HeadRoom:

www.headphone.com/products/headphones/in-ear-monitor/etymotic-er-6i.php

They'll give you $20 off the retail price of $149.

Sennheiser HD 457 - I found these the best compromise in regards of sound quality and bulkyness.

Shure EC-3 are the first in-ear 'phones I can live with (sound great too). The Ety's were way too uncomfortable... but everyone's ears are shaped differently.

I own the Shure E2c and have heard them against the E3c. The E2c has better bass extension while keeping the same great midrange and highs. The fit and style are completely different, though, and will depend on your ears. It appears to me the E3c and E4c were designed specifically with the iPod crowd in mind, while the E2c and E5c are carryovers from Shure's line for working musicians. The E4c and E5c are both supposed to be terrific, but were way out of my, and your price range.

I've also heard the Ety 6 and liked my Shures better. The Ety 4 is supposed to be great but again, out of our price range. If you're looking for a bargain, I'd recommend the Sony EX-71. I thought it was virtually identical in sound to the E3c, and can be had for less than $50 online.

I'll second or third the Shure E2c. That's what I'm using.

Plan A: Shure E3s w/ optional triple flange. Better fit equals better sound!

Plan B: Assuming (hopefully!) that you already have a set of nice full-size cans (e.g. Sennheiser, Grado), spend the $150 on a nice headphone amp (e.g. Headroom, Creek, JMT Audio). Rip your CDs in Apple's Lossless Codec (ALC) and begin to hear a whole new level of performance from your iPod!

Good luck.

Shure E3c.
Art

Etymotic ER-4P (for portable).

I had the shure E2C's, I thought they were ok, I was gonna try the Etymotic, but, ecost is running a special on the E4C's for 139, I bought those and WOW, big difference in sound quality. A great deal too.

Smilin

Do they need to be earbuds? If not, Grado SR60s are the obvious choice.

For those who do not mind something inside their ears, earbuds are great, but, there are many who never felt comfortable. It depends from person to person, trying out an earbud would be the logical approach before you commit yourself.

iPods are primarily portable devices and large headphones basically defeat the purpose of iPods portability. The supplied phones are below average if sound quality is high on ones list, one of the best compromise is to go for something like Sennheiser PX 200, I bought them and reviewed them. The link is provided for your reference.

http://www.epinions.com/content_190056009348

Good Luck!