[MrVinny1113]

I just upgraded from my Sony MDR-XB500s to the Sennheiser HD 558s and I was slightly disappointed when I first wore them on and realized they weren't as comfortable as the XB500s.
 
And then I wondered what the most comfortable headphones of all time were and I created this thread.
 
[Insert thread title here]

 

[Nhubley]

I looooove my HD700's. 

 

[So Far]

DT880 IMO

 

[SunshineReggae]

  DT880 IMO

yes they are very comfortable to me too, also had no issues with HD598, HD600 or DT770.

 

[Rhamnetin]

Stax SR-007, Stax SR-009, HiFiMan HE-560, which probably means the HE-400i too since it seems to have the same external design as the HE-560 (I've never worn one though).  
 
Why these?  Suspended headband design = feels practically weightless on the top of your head, and they don't weigh a ton either so they shouldn't strain most peoples' necks (HE-560 is particularly light).  On top of that, the pads go completely over my ears (I hate it when OVER EAR headphones still touch my ears *cough HD 650). The SR-009 has amazingly soft and comfy lambskin leather ear pads as well, and I think the SR-007Mk2 does too.  I tried the Mk1, both this and the HE-560's pleather feel authentic though and are almost equally soft.
 
The velour trim on the HE-560 pads is a plus for comfort in hot environments.

 

[Makiah S]

  Stax SR-007, Stax SR-009, HiFiMan HE-560, which probably means the HE-400i too since it seems to have the same external design as the HE-560 (I've never worn one though).  
 
Why these?  Suspended headband design = feels practically weightless on the top of your head, and they don't weigh a ton either so they shouldn't strain most peoples' necks (HE-560 is particularly light).  On top of that, the pads go completely over my ears (I hate it when OVER EAR headphones still touch my ears *cough HD 650). The SR-009 has amazingly soft and comfy lambskin leather ear pads as well, and I think the SR-007Mk2 does too.  I tried the Mk1, both this and the HE-560's pleather feel authentic though and are almost equally soft.
 
The velour trim on the HE-560 pads is a plus for comfort in hot environments.

Oh gawd yea, I tried the Velour Trim on the HE 560 pads... it was better than my DT 880 Velours I'm saddened to say. But the DT 880 is overall pretty awesome comfort wise
 
the LCD Vegan pads are also super comfy if you put them on lighter headphones [which I doubt u will] but honestly though, I thought the LCD 2 was pretty comfy! I wore the one I demo'd like 6-7 hours at a time 

 

[pbui44]

Denon D 400/600/1k/2k/5k/7k/7100
AKG K 550/551
Beyerdynamic DT 770/880/990
Sony MDR F1
Stax SR 007MKi/009(Space suit sold seperately )
Senneheiser HD 250/520/580/600/650/700
Hifiman (bend headband first) HE 4/5/6/300/400/500
Audio Technica W 1000X/5000

Fit may vary, though.

 

[Rhamnetin]

Fit may vary, though.

 
That's another reason why I vote for the SR-007/SR-009 and HE-560.  They can fit pretty much anyone.  Fit is a huge concern for the Audio Technicas.

 

[Aizura]

 

[Sundown]

Sennheiser HD700 is perfection on my head for comfort.

 

[AKG240]

Sony MDR MA900

 

[Fadem]

  Sony MDR MA900

I have the MA900 and I find that they don't entirely live up to the comfort hype surrounding them. The headband manages to put just the right amount of pressure on the wrong place for me to have to readjust the band every once in a while... Still, they're a lot better than those ultra-hard clamping, migraine inducing, headphones that some manufacturers seem to produce!
Another pet peeve of mine regarding these is that the drivers sometimes touch the tip of my ears depending on how I position them. Not sure if they deserve the title of "most comfortable headphones" due to these minor discomforts.

 

[BucketInABucket]

Comfort is subjective.

 

[xdog]

I would say that is the wrong question.
Because most comfortable over-the-ear headphones for me were some 8$ ones just because the headband got so streached that the cups did not touch my ears... (and it stayed on my head too)
Not to mention some very light on-ear-design, which you basically don't feel on your head.
 
Probably HD800, if you want to consider something high quality (much better than hifiman and old sennheiser stuff)

 

[Nhubley]

Try some headphones on!