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

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The Shokz OpenComm2 UC is probably the closest to your "unicorn." Because it’s bone conduction (sits in front of the ears), it doesn't press your glasses into your temples at all and is incredibly lightweight. If you need more range for roaming the house, the Poly Voyager Focus 2 is a great alternative, it's very "glasses-friendly" due to its plush on-ear design and has excellent noise canceling for both your ears and your mic.
I had an evolve 75 but the mic finally went in it so I switched to the plantronics VFocus2. I like them better than the Jabras .
Poly Voyager Focus 2 they're on ear rather than over ear, but are amazing sound quality for both you and the people on the call.
Is your ai assistant a piece of software running on your Mac or is it an unconnected physical device? If it’s a software device on your Mac then it should be able to intercept the call and hear both sides of the conversation. Teams with copilot does this fine regardless of headset you have connected. Personally I use the poly voyager focus 2, amazing headset, comfy, noise cancelling both for you and for the microphone so background noise is eliminated. Great wireless clarity and range using the provided dongle.
I like my Poly Voyager Focus 2. It's dual on the ear with noise cancelling. If the battery dies, I can still plug it into my PC to charge and it works while charging.
For Teams calls, I use a Poly Voyager Focus 2. For music, etc. I switch to my Sony WH XM6 or Buds 4 Pro.
The active noise cancelling with Bose is “too good” for my ears. I can handle it with AirPodPro, but had to give away my QC. Maybe the seal was too much?? They were very comfortable, aside from making me a little nauseated. (And they didn’t do that until I got older and have more ear issues.) I regularly use Poly Voyager Focus 2 for about 12 hours/day. They are on-ear. It took time to build my ears up to that. But now I forget they are on. My ears get cold without them! They have a boom mic that you can mute by pushing it up. Really good noise cancelling isn’t as important to me though. Oh! I’ve had them for 4 years and bought them used. About $300 now. I think they sell replacement parts, the company is geared toward office work.

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