[krrm]

My ranking:
1) DT880, can wear them for *many* hours without any problems
2) DT770, a little more clamp
3) Stax 202, comfortable for short sessions (better than 770), but get hot & clammy after about an hour.

 

[fordgtlover]

Senn 580s - like wearing little pillows on my ears (referring to the comfort not the muffled sound)

 

[jlingo]

GS-1000 very comfortable for me.

 

[jonnywolfet]

i actually like my e5c the best, once threaded down the back of my shirt, tightened just right with the slider and clipped into place they just dissapear! i guess its because im so used to them. my dt770 are also very comfy, velour is soo soft!

 

[RasmusseN]

out of the headphones I own

I'd say the HD555 and there in your price range

and I own the HD580 they clamp and feel bigger on the head.

 

[auris]

I was going to answer either Sennheiser 590s or '05 Beyerdynamic DT 880s (neither of which I currently own) . . . but when I thought about it, my old pair of Sennheiser HD-424X from the 1970s might be the most comfortable of them all.

 

[MaloS]

ksc75 - ack no.
Either loose on the ears or cutting into them, depending on the ear shape obviously, but not very universal.
Some of the iems are quite comfy, especially for those getting out of a grado clamp. (I don't feel the Vibe unless its cold out).

 

[John_M]

Bose QC2s.

 

[tonym]

GS1000.

 

[skaarse]

I dont know much about hedphones....but I bought some beyerdynamic DT 770 pro...They are fenomenal! In sound and comfort

 

[351Cleveland]

Sony MDR-CD780 with those giant gel pillows are the most insanely comfortable phones I've ever used.

 

[tanis38]

The most comfortable pair I have owned were my HD555's.

 

[Mortalcoil]

GS1-k

 

[alphaproject]

Sadly the Bose Triports were instantly comfortable while my good headphones usually require some break in time.

My DT 770's are getting more comfortable the more I wear them. The pads are big, but are a tad solid "new". Usually I like it when they wear in a bit to my head.

The triports would break though from the weak headband. Also....Bose...

The Audio Technica M50s felt nice and soft....they had a unique really soft leather unlike the hard M40fs ones I used to wear.

 

[Namrac]

My DT770's have gotten more comfortable over time, but they still can't touch the HD555s. So lightweight and squishy and soft. I'd have them on my head an hour after my music was off because I forgot they were there.