[heavyharmonies]

I'm a cubicle jockey by day, and tend to have headphones on 5-8 hours a day. It's amazing the sheer number of headphones that become outright painful over the course of an hour or two.
 
IEMs really aren't suitable for long-term continuous use, IMO, especially if you need to still be able to hear the phone ring, coworkers ask questions, etc.
 
I have a pair of Grado 225s, which are quite possibly some of the most excruciatingly painful headphones ever designed.
 
I occasionally try out other headphones, but at the end of the day, after 5+ years, I have yet to find a more comfortable pair of cans than my Sennheiser HD590. I can wear them for 8+ hours at a stretch and they never lose their comfort. Because they surround the ear without touching it rather than exerting any pressure on the ear, there is no long-term weight/pressure fatigue.
 
In fact I so lamented the possible demise of my 590s that I just bought a second pair on eBay for $70 shipped, just in case (buying backup headphones just in case the primary set fails; is that lame or what?). They arrived in gem mint condition; they look like they've never been used.
 
I was surprised to find that Sennheiser still sells replacement cushions for the 590.
 
So what are your faves for all-day use?

 

[anoldvolvo240]

225s on right now. i can wear them for hours. no issues.

 

[wae5]

"I have a pair of Grado 225s, which are quite possibly some of the most excruciatingly painful headphones ever designed."
 
 
I listen to the Alessandro MS1 more than any other phone because I like the way it sounds & for me it's my most comfortable phone.
 

 

[ex0du5]

I'm on the PC a lot at home. Often for 5-8 hours a day. The only headphones that have really worked out for me:
 
http://www.plantronics.com/images/catalog/product_fullsize/audio770.jpg
 
I'm quite angry that these are discontinued. While they are somewhat cheaply made and the boom mic doesn't stay up on it's own, they're just so comfortable in the long run. They are incredibly light, they have an open design, they have no clamp whatsoever, and you just cannot feel the headband at all with their design. Even the AD700 are uncomfortable in comparison. As a bonus, they have a very neutral sonic signature, with rolled off highs, which makes them even more comfortable in the long run.
 
I've been trying PC headsets and headphones up to the AD700 and K702, and still can't find anything that compares in terms of comfort and ease of listening.

 

[gregoire]

I too have a pair of HD590's and they are incredibly comfortable. I recently bought a set of Shure SRH440s to have a closed back option so i could turn the volume up more at work without annoying people with open backed cans, but i found them very uncomfortable after 2 hours. I then went for a set of Beyer DT770s and they are really comfortable, more clamping pressure than the 590s but still very comfy and i can wear them for around 8 hours a day with a short lunch break. 
I think for long listening sessions you HAVE to have a can with velour pads, pleather gets nasty very quickly.

 

[cheaphifi]

AKG K601

 

[monoethylene]

This one are the most comfortable
 

 

[olor1n]

HD650. Would also buy a second pair as backup if I wasn't so obsessed with speakers at the moment.

 

[vrln]

The most comfortable headphones I´ve ever used are the HD 800, and by a large margin. Sennheiser in general is fantastic in ergonomics.

 

[keanex]

My Ad900 are pretty comfy for extended use.

 

[Region2]

I'm still going to go with my Stax SR007 as the most comfortable headphones I've ever worn.  Lately, I've been using the SR404 for bedside use and have found I can sleep with them on--I was afraid I broke them when I woke up and realized they were still on.
 
In the office, I tend to alternate between the Denon D7000, Stax SR001, and AKG K240.  For the most part, I tend to put on the D7000 since I really like the JMoney earpads.
 
Then again, if I like the headphones enough I don't care how much they hurt my neck (for example, the LCD-2).

 

[hifidk]

I have tried many headphones and O2 and HD800 are the most comfortable headphones. T1, HD600/650, K601, D7000, AD900 are very comfortable as well, but not as comfortable as those two I mentioned. Headphoens like K701, most Grados, HE5, LCD2, K1000 were uncomfortable on my head. 

 

[Proglover]

HD650's are the most comfortable of the ones I have/had

 

[Speedv1]

Been wearing my Ultrasone Pro 750 for around 4 hours no - no discomfort!

 

[brasewel]

My LA2000s are extremely comfortable....the earpads dont touch the ears hence can be worn for hours on end.