Most comfortable around ear sports earbud i've found - Skullcandy Chops Flex Sport Earbuds

I don't like the style that has the rubber fitting that you have to jam into your ear canal, this unfortunately leaves me with a lot less options.

I have tried the phillips, JVC and Sony equivalents to these and did not like how they felt. I am allowed to listen to music while I work but cannot have both earbuds in; my compromise is to use these bad boys and not have them actually in my ear just hanging close by. With these they hang more pretty comfortably close enough to my ears to still hear the music yet hear what's going on around me(Much better than having one hanging down).

I also like the in line controls for skipping songs and going back/play and pause. To me a must have for work and skateboarding.

The main issue I have run into was that after a while when the headphones are worn out they start causing my phone to automatically turn down the volume constantly. This doesn't happen all of the time just once and a while but when it does it makes my phone unusable for music.

As far as sound goes they are about the same as all the other ones I tried, which is not bad.

These do have their flaws but I still find them more pleasant to use than the alternatives of the same style.