[Nothingpersnal]

800/800S is by far most comfy over ear for glasses users imo.

 

[halcyon]

Sony MDR-F1, nothing else comes close, but only if you can find them 2nd hand:

https://overearmania.com/2019/10/14/sony-mdr-f1/

 

[Levanter]

HD800S comfort/breathability >>>>>> HD6XX/5XX
You will still feel warm/hot with the HD6XX/5XX

If price is not a concern, there is also Mysphere 3. Since the earcups is not touching your ears at all, that would have the best comfort/breathability out of everything

 

[Prog Rock Man]

My default long term listening most comfortable headphones, are the AKG K271 Mkii, with fabric pads. Light, don't clamp too hard, and a smooth headband.

 

[P007]

What's your budget? As for comfort, absolutely lightest/easiest to wear have been Dan Clark's Ether headphones. Perhaps stay away from Audeze, as their headphones are generally very heavy. I found Sennheiser HD800 very light too. As you can see, for me comfort equals weight, but perhaps for you it is more the shape of the ear cup? Hifiman headphones are quite light too, but I found their comfort lack (pressing against my jaw). For Abyss, there my temples hurt. Others, like Focal I felt too hot in them

I would second the Dan Clark as having very comfortable headphones, but not as portable/easily powered since they are planars.

Try before you buy! Clamp force will be important.

 

[Xerath]

ATH air series is a solid choice in mid range , I think ath-r70x or ad series will be good for a long run. However they have an unique sound so I recommend you to try it at least once. Then like everyone say , Sennheiser is too.

But I don't recommend Audeze and most of Hifiman even how its seem to be comfortable tbh