Physically Comfortable Headphones

Thank you all for your headphone-comfort thoughts. It is funny - to a certain extent, I would compromise sound quality just to be able to wear the things without discomfort. It would be really nice if I didn't have to compromise too much. 

I tend to like a warmer sound - the pre-fazor LCD-2's are very close to my ideal, but the weight and the fit can be punishing. I tried the Sennheiser 800's and the treble response was a bit too much for me - though I agree that they were more comfortable than average.

I have a local dealer - Goodwin's High End - who are Hifiman dealers, and claim to have the Arya to audition. So, I think I will go see them and try them on. The trouble is that I need to sit there for at least 30 minutes to see how the fit works over time. I hope they have a sense of humor about that...

You also brought up some brands I knew existed, but didn't know anything else about, like Dan Clark and iBasso. I will start my auditions soon. 

I really appreciate the opinions. I find it helpful, as I usually do on this site.

David

While I no longer have them, I've tried a lot of different headphones, and the Meze Empyreans are for me the most comfortable.... 

I'm glad you're willing to go and audition the HifiMans. I would also recommend them. I considered myself a Focal guy until I tried the HE1K V2's and I was instantly converted. Liked them so much I made the considerable leap to the Susvara, which was another huge improvement. I hate to use such an overused term but these truly are "end-game" for me (and I got a pretty substantial discount off the $6K list price). They have so little clamping force that if you tilt your head forward or back they will fall off! HFM obviously placed a major importance on comfort.

I've had a few Audeze models and they're all just ridiculously heavy. Focals are much better. I've never heard the Utopia 2022 but it's the only other HP I would still like to. The Clear Mg is an excellent HP and in your price range. A little more clamping force than the Susvaras but I suspect that will be true for pretty much any other 'phones.

I use the McIntosh tube headphone amp. There's a review you can easily find if you Google it saying that, with a tube change (which I've made), it is the best HP amp the reviewer has ever heard (this is from an older, very seasoned reviewer) and I believe it's a fair bit less expensive than the balanced Woo Audio choices. Only caveat would be that I would try to have a DAC or preamp with a volume control because the one on the Mac is annoyingly hair-trigger. With that taken out of the equation it's pure bliss.

Definitely stay with open-backs. The best closed-backs I've personally heard are the Denon 9200's ($1600 and extremely well-made). I use them nightly so as not to disturb my wife and they are quite good but can't hold a candle to the Susvaras.

Sorry for such a long-winded response but headphone rigs are something I'm (obviously) pretty passionate about.

Another Sennheiser HD800 recommendation. Comfortable on my XL head, lighter weight than comparables, great sound and in your price range.

@yoyoyaya  - Interesting ("Sennheiser HD800 - much more comfortable than the 650s and extremely light"). I have used the Senn 650 for years and find them very comfortable. I will have to try out the 800 if I decide to upgrade.