[Lorspeaker]

bose AE2I has its place...unamped and on the go, its comfort and small compactness is great for road warriors.
The sound is quite balanced though it can use a little more bass mass. 
Compared to the kns8400...i would bring the Bose out to town.
 
Philips Uptown i s v comfy too..soft memory foam. 
Its got a bigger sound than the bose. 
its also sizeably bigger...without foldable cups.

 

[MorbidToaster]

I wish the ear cups were a little bigger but other than that they are indeed a very comfortable headphone.
 
Quote:

bose AE2I has its place...unamped and on the go, its comfort and small compactness is great for road warriors.
The sound is quite balanced though it can use a little more bass mass. 
Compared to the kns8400...i would bring the Bose out to town.
 
Philips Uptown i s v comfy too..soft memory foam. 
Its got a bigger sound than the bose. 
its also sizeably bigger...without foldable cups.

 

[MetalHealth30]

While I didn't particularly like them, my HD 228's were quite comfortable. Sennheiser just came out with the 239 I believe? I think the HD 239 is simply an improved, open back version of the rest of the 2*8 series, so maybe give them a look. They were the most comfortable cans I have ever owned.

 

[Dyaems]

sony xb series - most comfortable headphone, i could be wrong though
fa003/hm5 - the pads are soft, similar to sony xb series soft
cd900st - it just sits ontop of your head, it just disappears once you start playing music
hd800 - debatable but similar to cd900st for me. sits on top of your head, then it disappears
 
the denons are OK but when you move or shake your head even by just a bit, they will move and might fall off thats what i had experienced in a d2000. i have a long-ish hair and the d2000 is modded so it might be heavier
 
skip the grados, they are hit or miss when it comes to comfort.

 

[Ishcabible]

Are the CD900ST's really that comfy? The V6 started getting annoying after two hours.

 

[Dyaems]

yeh they are comfy since it has a light clamp and thin pads unlike the v6. also, it has this magic not falling off if you shake your head lol

 

[streetdragon]

hd598 is pretty comfortable too since their velour earpads are huge and very soft but if that is too expensive
the hd558 is also almost as comfortable (earpads are slighly stiffer) 
clampig force on both are not too strong

 

[theeyealtering]

AD900 and AD700 are probably the most comfortable headphones I've worn.

Not sure if the AD700 fits your taste, but it can be got for well under $200.

 

[obobskivich]

The Bose AE1/2 are bested only by the QC15 and the Sony MDR-F1; you can't buy the F1 anymore, so the QC15 get the nod imho. If it doesn't have to go out on the road, I think the Kenwood KH-K1000 are super comfortable as well (I regard them better than the D2000) - more expensive, and bulky though. Bit heavy too, again, they're very impractical for mobile use, but at home they're just sublime.

 

[livngston]

I am fine with either open or closed back.  My concern with the closed back over-ear is the pressure and ventilation issue.  I had the ATH-M50s and my ears started to sweat within 30 minutes.  I would go with an on-ear over that.
 
BTW for the Bose, I meant to refer to the OE2, not the IE2.  I already have the Klipsch S4 for my in ear model (which I love).
 
I don't see the D2000 on Amazon for less than $350, which is out of my price range.

 

[Ishcabible]

Someone bought the $200 D2000. If you can stretch $10, there's another used one. http://www.amazon.com/gp/offer-listing/B000MVEC0Q/ref=sr_1_1_olp?ie=UTF8&qid=1344951548&sr=8-1&keywords=d2000+denon&condition=used

 

[livngston]

I have been hearing good things about the Beyerdynamic DT770 (80 ohm).  How does that one sound compared to the ATH-M50?