Audiophiles hifi appreciation thread old and new

I think switching between in-ear and over-ear headphones would be a good approach.
I doubt you'll find something that's comfortable for 10+ hours, 6 days a week.

Good fit is important with in-ears obviously, so depending on what you're comfortable with use the squishy foamy things, the silicon things or plastic ones that just happen to fit your ear well and experiment with replacement cusions for those.

If open-back / sound bleeding into your surrounding is an option, then for over-ears I found both Grado SR-60's or Koss Porta Pro's very comfortable (and good sounding).

Something custom moulded?

Good fit is important with in-ears obviously, so depending on what you're comfortable with use the squishy foamy things, the silicon things or plastic ones that just happen to fit your ear well and experiment with replacement cusions for those.

ATH-R70x for listening to music
Use AirPods or similar when on calls.

the ever present squeeze on the glasses

Struggle is real

.

Fully agree with the problem of all day comfort - I don't wear glasses but hate how my ears get hot and sweaty with over-ear headphones. Definitely go for a wired solution without any BT compression / dropout issues etc. Wired are definitely lighter as no batteries etc.

Personally I've settled with on-ear rather than over-the-ear, I use Bower and Wilkins P5 which are light and keep my ears relatively cool. The P3s are fabric and even more breathable I think.

Otherwise how about the IEMs Steve mentioned upthread?

If its only for work calls / voice i say try aftershocks aeropex. I have used mine solidly for this purpose all through lockdown and they have been great. Its quite nice to be able to get up and walk about easily in calls.

They're not great for music or anything with bass, but for talk and general usage youtube etc they've been perfect. I get very sore inner ears from IEMs so its been a good compromise for me.

I see they do something for this purpose now:

https://aftershokz.com/products/opencomm

EDIT: Just seen that you dont want BT, which is fair enough but I will say I can stand on the opposite side on my flat 3 rooms away and talk without any problems with mine connected to my HP Elitebook. In fact on one extemely hot day this summer during a very long training session i had a brief cold shower with them on to cool off. I never have had a problem hearing anyone and no one complained about my voice but maybe thats just me.

I'm looking for perhaps the impossible.

Headphones / ear phones / IEMs that can be worn for 10+ hours a day, 6 days a week.

My partner has calls all day sometimes. For her, we went for a headset designed for all day wearing, eg, switchboard or reception work, rather than headphones for music etc. They do wired versions too. But it's really light and she has no issues wearing all day or with the sound quality.