[Marximus]

AKG K 601s or Bose AE2 are the most comfortable that I've tried.

 

[Makiah S]

  AKG K 601s or Bose AE2 are the most comfortable that I've tried.

That face, yea what ever Marximus is wearing in that pic must be pretty comfy! 

 

[butt]

Beyer T1.

 

[SunshineReggae]

T1 is not bad, but can have better results from other headphones.

 

[TWerk]

Comfort is extremely important to me, and I have sold quite a few headphones because they were not comfortable (GRADO I'm looking at you!!!)
 
Anyways, my D5k and D7k feel just about perfect on my head. Very comfortable and natural fit, with little clamping pressure. The headband distributes the weight perfectly across the entire head. They fit great.
 
Also, the Fidelio X1 is supremely comfortable, with the soft velour pads and the adjustable headband.
 
These are among the most comfortable headphones I've tried. Pretty flawless.
 
As I said, worst comfort award goes to Grados. Very cheap foam pads don't work. Just doesn't do it for me, and it's a shame since otherwise I enjoyed the sound of them very much.
 
The Ultrasone HFI 780 also was pretty uncomfortable. Squeezed the crap out of my head. Also, the headband pad on it was actually quite hard and stiff. Not good. Their pro line headphones are MUCH more comfortable with their velour pads and headband.

 

[SunshineReggae]

I can wear DT880 all day long and is zero issue. Difference between having them on and off is extremely small, except for the wire.
 
Most headphones from the past they were eventually annoying in some way, sometimes a little, sometimes a lot.
 
I used to own Sennheiser HD437, this one is also excellent headphone for comfort. You don't mind it at all.

 

[TWerk]

^ Yes, when I had the Bayer DT990, I found it super comfortable as well. The Bayers are very comfortable headphones.

 

[zazex]

The Beyer 770,780, and 990 are all superbly comfortable.
So are the AKG 700X series (without the bumpy headbands).
 
But, for my money, no headphone is as comfortable as the
Sony MDR MA 900.  It takes the cake.

 

[AnalogSavior]

HD598 is stupidly comfortable.  Light, very little pressure, ears don't touch ear cups...its great.  HD800 was great too, just heavier.  HD600/650 end up squeezing too hard and my ears touch the ear cups.  Not so good IMO (which is a shame because they sound great).

 

[kalrykh]

AKG K 601s or Bose AE2 are the most comfortable that I've tried.

I second the AE2 for comfort. It's like wrapping your head in a cloud of boobs.

 

[money4me247]

Comfort is NOT subjective!!! There are a variety of objective factors that can be considered when talking about comfort: clamping force, overall headphone weight, weight distribution over the headband, headband material, earcup material, and earcup depth & diameter. The importance of these variables to the user can be subjective.
 
Keeping these factors in mind, the most objectively comfortable portable closed pair of headphones that I have tried the Sony MDR-1R: Clamping force is not too tight, light-weight at 235g, weight is symmetrically distributed across the headband, headband and earcups made of pleather, earcup dimensions are 60mm tall, 40mm wide, and 12-22mm deep due to the angled driver.
 
There are only two comfort concerns with the MDR-1R.
1) The pleather material is beat by real leather of the Sennheiser Over-Ear Momentum (but the Momentum Over-Ear earcup dimensions so extremely small that are actually on-ears). Over-ears will good earpad dimensions will inherently beat on-ears as on-ears suffer from the pressure of the earpads ontop of your ears.
2) 22mm depth may not be deep enough to keep the edge of the ears of certain users off the driver.
However, in my experience, I have not found another pair of portable over-ear headphones with a deeper clearance for your ears, so the MDR-1R will still be the most comfortable option.
 
For open headphones, I personally found the Hifiman HE-560 to be extremely comfortable. Comfort specs for the HE-560 are top-notch as well. Clamping force is not too tight, light-weight for orthodynamic headphones at 390g, weight is distributed symmetrically due to suspension style headband, velour used in earpads, earcup dimensions are 55mm diameter with 20 to >25mm depth for the angled earpads. The Oppo PM-1 is another great contender for comfort with real lambskin leather used, but I personally think that the HE-560 suspension headband system edges it out over the PM-1. That is the subjective spin of which variable is more important to you personally.
 
I would love to see how other "comfortable headphones" match up against my two personal picks in terms of comfort-specs!!! I have not tried all the headphones out there, so if another pair of headphones out-spec my choices in the comfort department, I will gladly admit defeat. However, there is an objective systematic way we can measure comfort and I think that headphone manufacturers will benefit from approaching comfort with this mindset as well.

 

[TheoS53]

My Razer Tiamat 2.2 are insanely comfortable...but sound quality is rather disappointing

 

[Vixcross]

Hd700 is pretty comfy

 

[Rhamnetin]

  Comfort is NOT subjective!!! There are a variety of objective factors that can be considered when talking about comfort: clamping force, overall headphone weight, weight distribution over the headband, headband material, earcup material, and earcup depth & diameter. The importance of these variables to the user can be subjective.
 
For open headphones, I personally found the Hifiman HE-560 to be extremely comfortable. Comfort specs for the HE-560 are top-notch as well. Clamping force is not too tight, light-weight for orthodynamic headphones at 390g, weight is distributed symmetrically due to suspension style headband, velour used in earpads, earcup dimensions are 55mm diameter with 20 to >25mm depth for the angled earpads. The Oppo PM-1 is another great contender for comfort with real lambskin leather used, but I personally think that the HE-560 suspension headband system edges it out over the PM-1. That is the subjective spin of which variable is more important to you personally.
 
I would love to see how other "comfortable headphones" match up against my two personal picks in terms of comfort-specs!!! I have not tried all the headphones out there, so if another pair of headphones out-spec my choices in the comfort department, I will gladly admit defeat. However, there is an objective systematic way we can measure comfort and I think that headphone manufacturers will benefit from approaching comfort with this mindset as well.

 
Comfort has subjectivity.  We all have different sized/shaped heads.  The effects of clamping force are subjective: a headphone that clamps too hard on one person may not clamp too hard for someone else.  Someone might prefer a rather tight clamp, but someone else even with the same sized head might not because they might be more sensitive.  Some prefer velour pads, others leather, so that's subjective as well.
 
With that being said, I also partially agree with you.  I can't imagine anyone finding the HE-560 to be less than extremely comfortable.  It's lightweight and the suspension headband design does a great job making them feel even lighter than they are.  The pleather pads are very soft and authentic, and the velour trim is very useful in hot environments.  It's fully adjustable to fit basically all sizes.  Most peoples' ears will fit fully inside the cups (but this is a subjective factor, some might not care about this).  The HE-560 is one of my picks for the most comfortable headphone, next to the Stax SR-007 and SR-009 (just about every aspect I mentioned applies to these Stax headphones too).  I'm sure the HE-400i will be equal in this regard as well.

 

[Za Warudo]

I still find the HE560 a bit heavy. The clamp also puts some discomfort by clamping down on my glasses. Furthermore the ear opening could be taller. The HD650 would be perfect if it didn't clamp so much and the pads becoming rather warm after awhile.

MRD-1R is my pick with the pad depth, angled drivers, and light weight.