
Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

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Thanks very much for this detailed writeup! I reached many of the same conclusions about the XM5s that you wrote above. There were also other things that I liked more about the XM3s and XM4s. One is their slightly wider, flatter headband that was more comfortable for me to wear on an extended basis. I also preferred how the XM3/XM4 earcups attached to the frame. They felt and looked more solid to me as well as permitting those headphones to be folded down. Finally, I think the mechanical design of the XM3/XM4 earcup attachment just leads to a stronger, more modern, and more pleasing visual aesthetic in my eyes. The XM5s just look a bit more fragile and retro to my eyes.
Sony WH-1000XM4 are my daily driver. Great sound, awesome features, long battery life and foldable (not flimsy) with a case. Do not buy heavys, they are a money grab with bad sound.
I have an XM4 for a couple of years now and I can’t find a reason to upgrade anytime soon.
might be worth getting the xm4s if you can find them, never had any issue with the mic quality in busy city centres or buses personally.
I have xm4s that are very good, but snagged airpods max on sale a few months ago and I am not looking back. The ease of connectivity is the thing for me, also they sound great. If you aren't in "the apple ecosystem", I would look into newer Sony headphones tho.
I'm often switching between watching a video on my tablet, to jumping on a call on my computer, to jumping on a call on my phone. The seamless pairing is huge. You can pair XM4's to 2 devices iirc, but it felt clunky. I mainly use them for travel or deep focus time at home, and imo the active noise canceling and transparency mode is much better on the airpods max vs XM4.
Personally I find them comfortable. They are not as light as my XM4's, but not to the point of discomfort. The band and ear cups are much more comfortable than the XM4's.
I will have my XM4’s 5 years this summer. Zero issues still in perfect condition. Best headphones I’ve ever owned. I had studio beats prior that were trash.

Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Sony
WH-1000XM4
ANC king, durable, but unreliable mic and touch controls.

Sennheiser
HD 6XX
Legendary mids, durable, but narrow soundstage and weak bass.

Sennheiser
HD 490 PRO
Super comfortable, wide soundstage for gaming, versatile pads.

Sennheiser
HD 599
Super comfortable, easy to drive, wide soundstage, open-back.

Ranked #1
Sennheiser - HD 6XX

Ranked #1
FiiO - FT1 Closed-back Headphones

Ranked #1
Sennheiser - HD 560S

Ranked #1
Sony - MDR-7506

Ranked #1
Sony - WH-1000XM4

Ranked #1
Sennheiser - HD 560S