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've used several Sennheisers and I second/third/fourth the HD 490 suggestions in this thread. They're slightly bassier and more exciting than the HD600-series, and *very* comfortable. If you like the open-back sound I also suggest you try something Grado, for example the SR325x is in your price range and very good. I know they're not for everybody, plenty of people don't like their sound. But also plenty of people *do*, so I recommend you try them as they may just be your jam.

I've tried for years to like the HD600s including forcing myself to listen only to them and nothing else for a month. Still no go. I liked the HD800s just fine. But I love Grados. I have the RS1i, RS1x, 325x and original GS1000s. I like them all better than either of the Sennheisers.

Grado 325x will be good

Grado SR325x puts Sennheiser to shame. You will be amazed at the soundstage (3D sound). Unbeatable sonic value for games, movies, and music.

Grado My sr60e survived so much abuse over the past 5 years I honestly don't get how. Now the sr325x is even tankier My friends one day showed up to work with his dad's sr60c (Yes c) And they still work like a charm. He has driving them daily for 3 years.

I don’t have much choice but to buy blind. I’ve just been lucky that I like how they sound enough to *mostly* ignore comfort. That said, I have tried everything (even yaxi pads) for my Grado 325x and I just can’t make them useable for more than a handful of minutes. Even if I love their sound

The SR325x is an absolute beauty. It’s a significant improvement over my old MS1i, both in terms of build quality and sound clarity. The Grado sound signature is timeless and never fails to impress. They feel like a piece of art on my desk. Currently, I’m pairing them with my Topping DX3 Pro+ and the synergy is impeccable.

Love that SR325x, it’s the best execution of Grado so far!