Pondering the perfect iPod headphones

I'm not a fan of earbuds in general. The Apple earbuds that ship with the iPod are uncomfortable to the point of being painful in my ears. Some ears just aren't designed to have thinly-covered plastic discs sitting inside them. But I also don't like carrying around somewhat bulkier and less attractive over-the-ear headphones, so I've always had a hard time finding the perfect earphones to accompany my iPod.

Until recently, my favorite iPod 'phones were a set of Koss SportaPros. The SportaPros were a good compromise... decent audio quality, inexpensive, collapsible for convenient carrying, and an adjustable headband that allowed me to wear it behind my neck or just further back on my head, so as not to muss up my carefully-styled hair*. Then I graduated to the Senheiser PX100. Not quite as versatile as the SportaPro, but better sound. Still I tired of having my ears covered all the time and I wanted an easy way to engage in one-ear listening (walking around NYC oblivious to all sounds around you is not really that safe).

When Griffin came out with the EarJams,
I thought they'd be a good solution. I could use the convenient Apple-supplied earbuds, while having the benefit of the more comfortable and more secure in-ear fit. Alas, I was wrong. I didn't care for the way they sounded and they really weren't very comfortable.

I ultimately switched to the
White Fontopia® Headphones
(MDR-EX71SL/WK)
and have been very happy with them. They are a great bang for the buck,
look good and are very comfortable in my ears (your ears may vary).

Now Dan Frakes comes along and makes me consider switching – again. Based on his preview of the Ultimate Ears super.fi headphones,
I might just consider splurging for a set when they become available in June. Thin, detachable cables and the prospect of truly custom earmolds for only an extra $50 makes it very tempting. According to Dan, they sound pretty good too :) You can read Dan's complete first impression on Playlist.

I
can't remember if we've done an iPod earphone survey on TUAW before and a quick search didn't turn anything up, so how about you tell us which headphones you use/like/dislike and why?

*This is a lie. My hair is not carefully styled. I'm a pretty low-maintenence chic(k).