Physically Comfortable Headphones

I’d highly recommend these Hifiman Arya Organics. I have the prior Arya Stealth version, and with their elongated ear pads that do a great job distributing pressure they’re very comfortable and I can wear them for hours without fatigue. They’re also light, which helps further and they’re also fairly easy to drive so you’ll have lots of amps (including tubes) to choose from. I’d term my ‘phones as neutral, but I think this newer version has some added heft of their pricier models so may work well for you sonically, and you can certainly adjust the sound through your choice of amp. Anyway, just one option to consider.
https://www.amazon.com/HIFIMAN-Arya-Organic-Full-Size-Audiophiles/dp/B0C5RFXMM5

Here’s a review that does a nice job describing their sonic characteristics in case it helps…

https://soundnews.net/reviews/headphones/hifiman-arya-organic-review-comparison/

While I greatly enjoy my HeadFi system, it’s really not a substitute for my big rig so if I’m you I’d do everything possible to keep a dedicated listening room in downsizing. Hope this helps, and best of luck.

Get open back headphones so it is cooler.  I like the sound better anyway.  And, look for a set that has metal in the upper band that goes over the heard, then simply bend the metal a bit it to fit your head.  Finally, look for felt or fabric ear pads - much better than leather plastic.    

I have a big head as well. I am sure lots of folks can attest to that.😊

I have had a headphone system since the 70’s. Over the last fifteen years I finally went all out to put together a really great system. Among others I have Focal Utopia, Sennheiser 800s, Audez LCD 2, Ultrasond Edition 8, Denon 5000, Grado, AKG…. And many others.

I have had many DACs, streamers and many headlamps with these headphones. While this is off topic… the thing that completely changed the game… after decades of upgrading was the Woo WA5 headamp with Takasuki 300B tubes. Unbelievable power, rich, warm musical sound… every set of headphones were so upgraded it was miraculous… the differences between the sound of the headphones became much smaller because this headamp simply took charge regardless of the quirks of the headphones and made them sound great.

In comparing my headphones in this system (see it under my userID, under virtual systems), I would usually conclude the Focal were a tiny bit better sounding than the Sennheiser and all the others. But over the last three years I migrated again and an again back to the Sennheiser. They sound so good, they are big and open… but not heavy like the Focal, Audeze, or Denon. They are so comfortable… I can wear them for hours and completely forget I am wearing them.

My partner wears Sennheiser 350 all night every night (she sleeps during the day). Now, these would not be for you, because the fit snugly… and she has a small head. But the 800 series are really comfortable without the closed in feel you get with many others.

While I have not heard the Arya Organics,I can attest to the superb comfort & light weight of the design they are based on..I have the Ananda Nano’s,which are 1 level down from the Arya’s..The tuning is superb,very nuetral with excellent bass & good slam..
The HFM sound is no where near as warm & darkish as the LCD-2,which I owned & sold because their weight wasn’t a good match for my bad neck & upper shoulders..Never had any trouble with HiFiMan..
Another headphone I HIGHLY recommend for comfort,lighter weight & SUPERB,naturally warm,highly organic tone, is the iBasso SR-3 with the caveats that you change out the cable to one using Silver plated copper & give them several hundred hours run in before critical listening...The Bio Cellulous driver they use has that slightly dark,warm tone similar to the LCD2 & the silver over copper cables opens up the treble just enough to add a touch of detail & transparency to the tone..I have the original Limited Edition SR-1 with upgraded cable & the tone is absolutely glorious,dripping with honey rich,golden glowing tonal colors,extended,tight bass & just enough on the top end to bring out low level detail without ever being harsh..I liken their tone to the finest 300B SET amplifiers...
Check out reviews of any headphone on your short list at head-fi.org.....