Headphones that don't hurt my medically altered ears?

Have you tried using foam eartips like those from Comply?

Also, the only headphones I've tried that don't actually touch my ears at all are the Sennheiser HD595 - they might work for you.

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On a serious note though, which around ear headphones have you tried? Have any of them caused you pain?

Well... I would recommend looking into the Sennheiser HD598/558.  I've found these to be sinfully comfortable.  In some cases I've actually found them to be a bit loose, and the sounds is quite nice as well. 

Quote:

Originally Posted by MegaMushroom 

Well... I would recommend looking into the Sennheiser HD598/558.  I've found these to be sinfully comfortable.  In some cases I've actually found them to be a bit loose, and the sounds is quite nice as well. 

I had HD558 and didn't find them that comfortable. The velours made my skin itchy and the clamp was quite strong.

What kind of sound signature are you looking for? If you want something bassy, check out the Sony MDR-XB700's. They are huge, but absurdly comfortable. In fact, since they are so big, there's more surface area on the pads to spread out clamp force.

I have the Sony MDR-XB500 and the Ear Cushions are big but really soft! They're Over-Ear too so they won't be physically touching your ears either (unless your ears are bigger than mine).

You might want to get the Sony MDR-XB700 instead though since the Ear Cushions are even bigger.

Like others have already suggested, I think you need to check out the Sony MDR-XB series. Minimum XB500, but I think the XB1000 would be better. Check them out in this thread: http://www.head-fi.org/t/533810/sony-mdr-xb1000-new-omg

If you go on ear, the Phiaton MS400 is untouchable, it can be bent outward to achieve almost no clamp at all and combined with its very soft earpads you can get great comfort, as can the ATH ESW9.  Both are excellent headphones.  

I feel you, Skyblue.  I had an ear infection when I was very little that left me with added pressure in the eustachian tube of my left ear.  I do NOT recommend the lauded Audiotechnica ATH-M50s, as they were extremely painful to me due to clamping pressure, and I had to return them almost instantly.  I personally have found AKG's offerings to be among the most comfortable, as most of the "clamping force" is distributed over the top of the head with the headband rather than resting directly on the ears.  Some of the higher-end Sennheiser models and even the Denon Ah-DX000 are quite nice, IMO, for both comfort and sound.  I hope this was helpful to you.

I have found the Denon DX000 series very comfortable.  I wish you the best with your search!

Surprised no one has suggested the Audio Technica AD series. Practically no clamp and many people would probably say they are some of the most comfortable out there. I thought my AD700s were really comfortable, just not enough clamp for me personally and it always felt like they would fall off.