I experimented with a good number of headphones in the past few years and I finally settled on two headphones that really stand out above the rest.
For sound quality and comfort, the
Sony MDR-D777. For in-ear comfort, the
Bose In-Ear Tri-Ports. I get my fair share of traveling by plane and found that even though the Sony headphones are not noise canceling, they do a good enough job of muffling out the engine noise and any other unexpected (screaming baby) noise. They do no have a great bass response, but for mids and highs, this is a superb set. Jenn bought these for me for my birthday after I tried them at a Sony Style store last year. They are amazing and I thank her every chance I get, even now. I loved them so much that I bought about 5 pairs and gifted them to friends this holiday season, including a pair for Jenn :) I actually slept on a plane with them on, which says a lot since I never sleep on planes!
The tri-ports were a shot in the dark. They claimed great Bose sound in a comfortable package. I will concur with the comfortable package. They do not give me the same amazing experience with my music that the Sony's do, but I can wear them all day long and not feel any pain or discomfort in my ears. It's worth the $99 for comfort, but not $99 for sound quality. They also let in a lot of ambient noise so they won't work out too well on a flight.
Previously I used the
Sony MDR-V150 headphones. They don't reproduce good sound quality at all and after half an hour of wearing them they are painful on the ears.
I bought a pair of
Logitech Wireless (bluetooth) headphones and found them to be both uncomfortable and cumbersome to use.
I am replacing a pair of
Sony MDR-EX51LP in-ear headphones with the tri-ports as I lost the ear canal cushion while walking around NYC and they also become extremely painful after twenty minutes in-ear.
Lastly, I want to mention a pair of headphones that JC bought for me two Hannukah's ago (that's right, I said Hannukah). They are the
Phillips HS310 headphones. I use them while at the gym and they are very comfortable but are no longer manufactured by Philips. They offer much less than the tri-ports for sound quality, but are almost as comfortable.