
Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.
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I have the same problem. For reference, when I wear bike helmet, I wear 62cm. Baseball cap size is XL or 7 3/4. I currently use Nova Pro 7, but the mic quality is not the best, and the sidetone has static noise. I have been using it for 3 years and looking for new one with better sound quality, mic and sidetone. Prior to this, I was using Sennheiser HD 598cs (same as 569), it's comfortable, but mic wasn't great and its wired. Here are the headphones I bought and returned due to small size. (either too tight or don't cover my earlobes) Logitech G Pro X2, Astro A50 gen5, Turtle Beach Stealth 700, EPOS H6Pro open, HyperX Cloud III, Nova Pro Wireless , Nova Pro 5. Drop PC37X, Sony Pulse, Sony Pulse Elite, Sony H5 Inzone. The only one that fit my head comfortably is Asus ROG Delta II, but the app is too buggy and sidetone didn't work for me.
I haven't used a gaming headset in about 15 years. Went from Sennheiser HD298s to Sennheiser HD558s, to my current cans, Sennheiser HD6XXs with defenestrated sheepskin velour cups. They're incredibly comfortable and despite daily use for about 5 years and a total of 5 house moves, they're still holding up with zero damage. I've paired all three sets with Antlion Modmics and have never been let down. I goddamn love this setup. Congrats on the killer set of cans, OP (phrasing)
I wear my Sennheiser 598 (open can) for like 16hrs in a row with glasses on sometimes, and they remain comfortable throughout. My ears get kinda uncomfortable if I wear my 598C (closed can) for more than a few hours in a row
Sennheiser HD598. I think I got them on offer for around £150 a good 15 years ago. They opened my eyes (ears) to how headphones could offer greater fidelity than HiFi speakers at a much much cheaper price point. I've since upgraded to the 6XX which is a clear step up for music even if not quite as comfortable. Seeing the 599SE on Amazon for £99 today makes me happy that a lot of people are going to be experiencing that same feeling for the first time.
Can’t say I’m familiar with them. I’ve just tried the HD600 and really liked them. I personally have been using a set of HD598s for about ten years and really loved them with no intent to upgrade. The HD600 is generally considered sort of the headphone for accurate sound reproduction. At that point the choice is going to be preference. I’d be seeking out everything I was considering and trying them out to see how I personally like them. Both sets are going to be similar quality in most ways.
Sennheiser 598SR headphones bought 2017 Pleather earpads and headband flaking. Earpads are easily changed out and wrapped the headband with grip tape. Both done twice.

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