Do you use your headphones for music, games, or movies? What genres do you listen to? Do you have any material or build quality preferences?
$800 is most likely the sweet spot for sound quality, if you go wire connection that is. IEMs would be the best bang for the buck in terms of sound quality, but in turn you are going to compromise a notch of soundstage.
I'm not sure how much you prefer sound quality over convenience. Because it seems to me you prefer the convenience of wireless connection over sound quality. On the bright side, if you do choose to go wire connection, apple products are driver-free so you can just plug and play with a DAC, since you might not be able to drive the sound out of some headphones with just a MacBook alone.
I personally really like Focal as a brand in general. I haven't tried their wireless ones yet, but their headphones usually pack a punch, and I really like that. Given your budget, I'd say Bathys is a no-brainer since its wireless. AirPods are dry as overcooked meat anyway.
If you're keen on "sounding good", go get a dedicated DAC and go wire connection with Focal. Clear Mg is their mid-tier headphone, but I personally think it is the sweet spot given your budget and diminishing returns. I tried it in person, and it really has that "wow effect" even though it is not even Focal's flagship.
I'm not sure what genre you usually listen to, but Focal is a safe bet since their headphones are very musical.
Try [https://www.focal.com/stores](https://www.focal.com/stores) and see if there's a store near you. I really think you should go try them out in store, since wireless models usually don't sound as good as the wired counterparts for some reason. The wired ones are the safer bets if you don't have a retailer near you.
I fly a lot and got my headphones here and there, so I don't really have a preference for audio shops. Go for the big ones if you are skeptical.
Focal Clear MG headphones paired with a JDS Labs Element IV DAC/Amp. That’s my home setup and it rips. For the office/travel/etc., I have Bose QC 35’s which are perfectly fine and super convenient.
I also recommend the Arya Stealth or similar headphones for wearing with glasses. On my previous headphones and others I've tried (DT880, DT1990, Focal Clear MG, HD490 Pro) I had to put the temples above the ear cups or I had exactly the issue OP has. The Arya's I can wear all day without issues.
I assume that the difference maker is the square headband combined with the strap that sits on your head and the very big cups, so the pressure towards the side of your head is greatly reduced/spread out.
AfterEye8775
