What are the most comfortable headphones or earbuds you've used?

I am using Beyer Dynamics DT-770 for recording and Beoplay H6 for "casual" music listening. Both are over-ear, extremely comfortable for me, both in terms of sound and wearing. Never got painful or tiresome, which happened after a while with pretty much all other over-ears I've tried.
 
My vote is for the Hyperx cloud earbuds here, great sound, battery life and comfort. Passive noise through works well too. That being said I have just bought my wife a set of Band & Olufsen E8’s and they really are very good, the sound is exceptional as you would expect from B&O. Though i would also recommned to see a few more such quality earbuds options like Jabra elite etc. Though apart of all these options and our own liking, the most important is your requirements and how would like to listen to the sound.
 
Our band started using the KZ ZS10 Pros, WE LOVE THEM!!

I have a $600 custom mold pair of IEM, the KZ's BLOW them away!
I feel so bad for spending the money on that custom set. But that was 2 years before the KZ's came out.

NOW the big tip here is Comply Memory Foam ear tips.
The most comfortable I have ever worn.

Check Amazon or the store. Amazon didn't offer what I was looking for but the Comply store did.

https://www.complyfoam.com/store/
 
My son's Razor Kraken X. Not pro sound, but the most comfortable I've ever put on. I could wear them indefinitely, even with glasses.
 
When I first got a set of ATH-M50s, they smashed my ears a little, so I got some replacement ear cups from somewhere in an Amazon review. Those really became all day comfortable earphones. Eventually the cups wore down, but it took years.

I think my DT880s out of the box have the clearance to be comfortable, but the clamping is stronger. I don't know what it is about them, maybe the sound itself, but I don't find I can wear them for more than two hours before I just have to take a break from them.

So right now, I have nothing really comfortable. I might give a pair of nicer Sennheisers a go.
 
Well it's way too late for the OP (hope he was happy with the HD280s). I found the HD280s to have a fairly tight grip and not really be that comfortable. In my opinion, nice, open backed, big headphones that don't rest on your ears are the most comfortable. My Sennheiser HD580s are pretty nice, much better than the 280s, but there are probably more comfy sets out there. On the other hand, a lot of it comes down to the shape of your head and ears, so YMMV.
 
I am wondering about the KZ12's and KZ16's that have come out since the 10's. Do you have any knowledge of comparisons?

I do not. Again I'm really SO satisfied with the KZ ZS 10 pros with Comply Memory Foam tips! :)
 
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