[bcasey25raptor]

Shure srh940 no doubt.

 

[daniloreyes]

+1 
The bose AE1 are really confy, not the best sound though.
The Sennheiser closed HD are confy but make you sweat. The Grados SR with small open pads (sr225 etc ) suck, and the PS1000 weights a ton, while the Grado GS1000 are really confy.
 
 
 

 

[Draygonn]

DT880's are amazing. HD800s are even better.

 

[nehcrow]

AD700 and SRH840!

 

[vid]

The Beyer DT231s were maybe the most comfortable. The vintage DT990s are pretty nice as well, though I don't have the original headband anymore and the pads have lost their fillings, so who knows how comfortable they were originally.

 

[lee730]

Denon 5000s . I think the Denons are winning this battle lol.

 

[vyyye]

D2K's, then again it's like the only headphone for more than $60 I ever used. Did try the HD650 once and that was nowhere near as comfy, felt like it was testing how much pressure my skull could take before imploding.

 

[joelpearce]

I have to chime in for the MDR-F1 as well, but I'm also surprised that the PX100 has only been mentioned once.  

 

[Canadian411]

I had Beyerdynamic DT990, Denon AH-D2000, AH-D5000, AH-D7000 and LCD2,
 
Most comfortable headphone is Sennheiser PXC450.
 
If I rank them, (higher the more comfortable)
 
1. Sennheiser PXC450
2. Grados
3. Beyerdynamic DT Premium series
4. Denon AH-Dxxx
5. Sennheiser HD800
.
.
.
100. LCD2.
1000. Dr. Dre Beats Pro

 

[fabio-fi]

The most comfy phones i ever worn: 
HD800's, HD598, and Beyers (DT990)

 

[pockits]

Sony SA5000....Beyer DT 990 and T1
 
 

 

[Windsor]

In terms of physical comfort, of what I've yet worn, I'd say that the Sennheisers have been consistently comfortable: The HD 800, the HD 600/650, and the HE90 are all very comfortable headphones. When I had the HD 6x0 headphones, I was amazed at how often I forgot I was wearing them. They are quite light and just became invisible on my head. Transparent headphones in more ways than one.
 
Also, when I tried the Sony R10 I found it really comfy - the leather pads were very soft and luxurious and it was quite light on the head.
 
In terms of sonic comfort, the HD 600/650 and LCD-2 top my list.

 

[SpiderNhan]

Oddball post of the thread:

Philips The Stretch

 
That inner headband just contours to the shape of your head and they're so damn light. Granted, with the exception of the Bose, Beats Studios and Sony XB500s, I have never seen or heard any of the headphones mentioned here in person. I'll give another vote to the XB-500. Those were really fun to wear.

 

[brokenthumb]

1. HD650
2. D2000
3. SR80i
4. K701 (Those bumps are killer)

 

[TheReallyCool]

I've gotta go with my k550s on this one. The clamping force is light, but just hard enough to make it feel secure on my head. I've been wearing them for 5 hours straight today with no discomfort whatsoever. 
Granted, I'm relatively new to this so I haven't tried on a very large number of headphones.