The biggest problem is Bluetooth itself. It’s just the worst wireless communications protocol ever invented. To go into the details here would involve writing an entire dissertation.

Outside of that, only one model from one brand has had proper head clamping pressure for me. That’s the Bose QC series. The QC 35 is the gold standard here, but sometimes it almost falls off my head. The QC 40 didn’t fall off my head as easily, but was more painful. Everything else is like putting your head into a steel vise. Sadly, where the Bose QC line has always faltered is on the audio side, even when used as wired headphones.

Good headphones also need to be able to be charged while they are also being used, if they have a battery. That has only now started to be solved by some models. Most still get this wrong.

IMO, don’t waste your money. Almost all of them are a complete waste of time and money, so do yourself a favor and just avoid the entire category. Go back to wired headphones. If you need a microphone, then try one of the wired gaming headsets that includes a mic. Find something that doesn’t break your skull with weight or head clamping force.

For me, one of the best solutions in this space is the HyperX Cloud II wired headphones. It’s not perfect, but it’s better than 99.9999% of the Bluetooth headphones I’ve tried, with regards to comfort and the ability to use it long term without too much pain or exhaustion. And since it’s wired, you don’t have any of that stupid Bluetooth wireless crap that ruins your day/week/month/year/life. And there’s no battery, so you don’t have to worry about charging them.