Grado - SR325x

So, there is a lot to unpack here. 1. AirPods Pro are actually great sounding earbuds, so you’re starting from a good place. 2. You’re right to move away from the APMs and XM4/5, although you may enjoy the Apple sound. Bang for the buck, it’s good about tech, though, not sound. 3. You can do a LOT with just wired headphones, if you’re OK with that. Not all of them need amps. A great example is the Grado sr325x: great sound, easy to drive. There are plenty of others in the wired world worth considering. If you prefer bass, for example, the Meze 99 Classic or 99 Noir would be good. For something more neutral, the HifiMan Ananda. All of these work great with just a $9 Apple dongle. And even if you DO need an amp, something like an iFi Go Link Max would fulfill any needs you have with modern headphones, so a Sennheiser 6xx + one of those would get you where you want. 4. If you’re dead set on wireless, check out the Sennheiser Momentum 4, the Bose QuietComfort Ultra (which often sells for under $400), and the Bowers & Wilkins Px7 S2 or S2e. (The S3 comes in at over $400.) All of these have decidedly different sound, and it will depend on what you like. Given your experience with the AirPods, the Sennheiser is probably your best bet. 5. Finally, for $350, you can find an incredible IEM, which might get you exactly where you want: the best sound for the money. But “best” is very relative here, since physics starts to play into the overall picture. Best of luck!

Grado SR325x I know its not exactly what you want but its probably for the best if you get some high quality open backs, open backs would be better if your like going on walks, getting groceries or doing things around the house or just a place you should kind of be attentive to around you, the Grado SR325x would be great for that, theres high quality, good build and you could even use them for studio listening, they are extremely portable seconded to iems and wireless headphones, and i also see lots of people buying them to use with walkmans. But Rode NTH-100 If you really want closed ear noise damping portable headphones, the Rode NTH-100 would also work, ive read reviews and it looks like they leak audio quite a lot but if you want the feel of fully over the ear headphone they look great for the price

i really can recommend my ie600 for this record, enjoying it with my Grados and Maxwell as well.

The headband on Grados are made from thin metal inside the faux leather exterior and you can bend it out of shape really easily to make it as tight or loose as you like. Mine pretty much sit over my ears and don't squeeze at all.

Grado 325x will be good

That’s why you need AT LEAST 10 sets of headphones! The only over/on eras I can wear individually are my 25 year old Grados. The only thing that prevents me from gluing AirPods Pro permanently to my head is battery life.

The nyczaj pads on those grado x drivers make them so good

Im an audio guy and after many years of optimizing playback solutions imo there are two very clear answers: Sennheiser 6XX for full size, and Etymotic ER2XR for IEMs.  The sennies can be found new for around 200 and the Etymotics are around 130 new. I found them uncomfortable and the cables are definitely microphonic but you can get aftermarket tips. For pure $/sound i think they are the strongest I've ever personally heard.  Another outside option is Grado SRs, for under 100 I love the sound. Build quality and comfort is meh but they look cool and sound excellent. They aren't a great match for every genre though, read up if interested. 

The DT 900 Pro X headphones are absolutely fantastic. Before getting them I had used AKG K550 Mk 2, AKG Q701, and Grado SR325e headphones, all of which are great, but I like these Beyerdynamics most of all. The soundstage is not as wide as the Q701s, but it has far better bass response than all of the above and has great clarity in the upper mids with good but controlled treble. The fact they don't take much at all to drive is a boon, too. The clamping force is a bit much at first and can get uncomfortable, but a bit of mild stretching sorts it out. Now I can wear them for many hours without a problem. For around 200 euros the quality of these cans is just incredible. Definitely better to get a good pair of dedicated headphones instead of a set of gaming ones. There probably are some decent enough ones out there somewhere, but if you want reliability and the best sound quality for the price, then you need to invest in some proper cans.

My 325s are perfect