That's very subjective - some people really like over-the-ear headsets, I prefer the in-ear variety. Basically, it's horses for courses.
The most comfortable set I've had were by Shure. They were super comfortable and had superb sound but they were very expensive (for a tightwad like me ) and sadly, the cable kept fraying. Think I had 4 or 5 replacment sets before I gave up.
I currently have MEElectronics S6 which are fairly comfortable, sound fine, have lasted pretty well (about 10 months so far - touchwood) and were reasonably priced. I got the model with a mic which works OK, too.
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