Thought I’d give my 2 cents:
As you can tell, there are a lot of factors that matter when it comes to comfort. Preference is above all of them, but you must know what your preference is… and if you haven’t tried at least a couple of different headphones, you can’t know what your preference is.
To help you out, these are some of the questions you need to find the answers to:
- Do you want oval, round, or special shaped ear-pads?
- Oval ear-pads are very good if you have average/normal ears, they are also better if you have taller ears. Round ear-pads are good if you have smaller ears, they are also better if you have wider ears.
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Do you want a relaxed fit or a tight fit? A relaxed fit can be worn forever if pulled off right, but it also won’t stay on your head if you bend over or rock your head to music. A tight fit will improve sound isolation, but if too strong, it can cause fatigue.
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Ear-pad material. Each one has its pros/cons. I found velour and fabric-like ear-pads to be the most forgiving when it comes to long-term listening sessions.
These are the 3 most basic questions you need to know the answers to.
Personal recommendation: Sennheiser HD598. Oldie but goldie. Unlike the new models from Sennheiser, this headphone has a relaxed yet “tight enough” fit, velour pads, and it’s lightweight. Nothing has beaten this headphone in terms of comfort, and I’ve had this headphone for 6 or 7 years (tbh I’ve lost count of how long I’ve owned it). I could wear this headphone for 24 hours and I wouldn’t have the need to take it off.
For example, that’s not the case with the “new” 6XX. It not only has a very tight clamp, but it also has firm ear-pads. It doesn’t come close to how easily the HD598’s disappear on my head.
Hope this is of use to someone!