About half the time I'm operating on HF I'm wearing headphones. Usually it's because I'm participating in a formal net - MARS or SHARES - and I need to be able to hear and acknowledge all participants, even under tough propagation conditions. This means headphones.
Like so many old-timers in Amateur Radio I've tried a huge variety of brands and models of headphones. All were good in some form or fashion. Some were really good - Heil headphone audio has always been universally good. I've owned some Bose and Sony 'studio reference' (whatever that means) headphones that were quite good, but they are designed more for listening to music than the spoken voice; too much bass and too wide of a response that can actually make voice communications sound 'muddy' to my ears. Great for listening to Beyoncé's latest over-produced off-key extravaganza, not so good for trying to dig callsigns out of the S7 noise floor.
Some of the best headphones I've used are not headphones at all. These are C. Crane earbuds. Crane builds them to emphasize voice communications, and they work great. They are my go-to 'headphones' for use with my radios during portable operations. The other good thing about Crane's earbuds is that they are cheap - about $20 a set. This means I can buy them in bulk so when my dog chews up a set I've got another sitting in the drawer ready to go.
But in my shack, when operating on HF, my long-time go-to headset is the classic Kenwood HS-5.
Kenwood has been making these headphones probably longer than I've been a ham, and you can't get more old school; an on-ear design, vinyl covered dual spring-steel headband, lots of cloth sleeved wiring, and a long obsolete 1/4" single ring audio plug. Plop these on your head and your hand starts instinctively reaching for a CW straight key. They are that old school.
But the Kenwood HS-5 'cans' (an old time term for headphones) do two things better than most. First, they fit well. They may be a bit heavier than modern all-plastic headsets, but they are very comfortable on my oversized noggin. They balance well and you simply don't notice the weight. But most important, they sound great! Easily as good as any Heil product I've used, and perhaps a bit better. Kenwood set the response on these headphones to emphasize the spoken voice (vs. a broader response for 'studio' headsets). I hear voices on HF better with these 'phones than most others.
Some folks complain about the 1/4" plug, and I guess that's a valid gripe, but there's easy fixes out there. You can buy a 1/4"-to-1/8" adapter on Amazon, or you can simply clip off the 1/4" plug and solder on a 1/8" plug. But I don't want Kenwood tinkering with the design to 'improve' them. There's no updating necessary. These headphones are a wonderful homage to the days of classic ham radio, when you had things like external VFOs and tube finals, and they still work great in today's modern SDR world.