Physically Comfortable Headphones

Meze Empyrean have come down considerably in price since the 2nd edition came out. With a bit of luck you may find one for around $1,500. I had Audeze LCD 2 before moving up to the Empyrean’s and couldn’t be happier. Very comfortable too. if you liked your LCD 2’s you’ll love the Empryean’s.

Oddly enough...I have a pair of Austrian audio Hi-X25BT that of the 8 plus sets I have (Sony, Sennhiser, AKG, etc)...are the most comfortable for my long / narrow head. Not the very best for listening, but for longer sessions of mid volume listening they are exceptional. 

I have the same problem - headphones are uncomfortable for me. I can tolerate the HD800S reasonably well, but every other headphone is a no-go comfort wise.

I recommend trying a decent set of IEMs. They have come a long way in terms of sound quality, rivaling headphones. I currently listen primarily to the Nightjar Singularity IEM, which has phenomenal sound quality that’s close to the HD800S in terms of enjoyment. MusicTeck and Bloom Audio sell a wide array of IEMs, including ultra-high end ones. Headphones dot com also sells a wide range of IEMs and allows you to return them for a full refund. Thie Audio and Elysian Acoustics are two well-regarded IEM manufacturers that you might want to read about and consider.

Thank you to others who have added since I last checked in. When you mention a headphone, I look it up, and read about them. From the humble Pioneer (found on ebay for $100) to the Hifiman, Meze, Dan Clark, etc etc, which are, well, more than that. 

Two of you mentioned IEM's and I sort of realized that amongst my favorite head-fi experiences are my Audeze iSine 10's. My ears don't get hot, my temples do not get pressed, they are not heavy. The iSine 10's are no longer made - in fact, I think that Audeze stopped making that line of in-ear earpphones. I think I would like a more refined version of the iSine 10's as a daily headphone, and will certainly pursue the in-ear solutions. I very much like that the iSine's do not require a seal in the ear canal - the business end simply delivers the music to your canal - it doesn't need to seal it to make deep bass. I like not needing to be closed off from the world quite so much. 

Again, I appreciate the suggestions...

David

I am surprised to not have seen STAX "ear speakers" mentioned.  They are light, open back and sonically speaking are extremely accurate.  I worked as an audio engineer and used Sennheiser 600 earphones for convenience during the recording sessions but used my STAX "Lambda Pro's" for editing purposes.  Their light weight often fooled me into thinking that I wasn't wearing earphones at all !