This is a difficult discussion to have, but it does come up often and I know there are always people out there looking for just the right kind of advice. I can only offer what my experience has offered me. I did go through a phase where I was buying headphones after headphones, looking for just the right quality of sound. Here are a few things to consider.
Number one: If you are in need of, want a pair of, and are only seeking wireless headphones, nothing you read about any of them will matter. Yes, some may sound better than others, but expense likely won’t make a difference. Let me tell you and listen closely: THERE IS NO SUCH THING AS WIRELESS HiRes. Once you go wireless, you cut off sound quality. Yes, some may still sound good, but you will not get the full experience going wireless. Not to mention if you are looking for wireless headphones you are probably listening to music from an app on your phone and you will absolutely not get HiRes that way. Don’t listen to what Apple Music and Qobuz have to say. Phone + wireless headphones does NOT equal optimum quality. End of story. If you must, don’t spend too much. And don’t believe the reviews online. Most of that is nonsense.
Number two: If you are going to do this the right way you will need a.) wired* headphones and b.) a HiRes music player. I cannot offer you better choices in the department of HiRes music players than FiiO or Astell&Kern. Hard to go wrong with those. Still, READ THE SPECS before you buy – and be sure to pay attention to the full variety of options available, even with just those two companies. Also, being someone who once had a large collection of headphones, at the end of the day I sold them all except two. Yes, all of them expect two. I kept my Focal Clear MG (though there are better Focal headphones you can get) [update: if anyone does get Focal headphones for a HiRes music player, you may find you will need upgrade cables. Please shop around. Search engines will point you to the most expensive ones and there are many more affordable upgrade cables that are just fine.] and I kept my Grado RS1x. Those two have been all I need. If I were rich I would get the Sennheiser HD 800S Dynamic Open-Back headphones. Those are really the only other headphones I have the slightest interest in. Perhaps one day in the future I will be able to get them. My point is, don’t make the mistake I made and go through all the fuss of trying many headphones seeking that perfect sound. Getting just the right headphones from the start will be best. But, again, without a HiRes music player or HiRes albums, you don’t need expensive headphones anyways. So, don’t waste your money on badly written reviews, because I am telling you – no matter how trustworthy a music related reviews website seems, they all lie. They are all full of it.
If you insist on just listening to music from an app streaming service you can still get good headphones and since you are likely listening on your phone you might as well go wireless. Don’t spend over $400. Really, it is criminal to be spending that much for wireless in the first place, but with the market being what it is you could very easily find yourself doing just that. I’m not going to tell you what to get if you are in this situation as it will all come down to personal preference and the quality of the sound between one company or another will all be in your head. (Still, I will offer that it would be in your best interest to stay away from Sony despite the claims they make about their technology or the raving reviews they get. Just a fair warning. Go ahead and waste your money if you must. You are free to be a fool.)
One last thing. If you are looking for IEMs instead of headphones look closely at FiiO. They have a large range of available options, some less expensive than others. Every pair of FiiO IEMs I have listened to has been just awesome. I did sell them all except for my FH9 IEMs, because, really, those are so good I didn’t want to listen to the others anymore. Still, the far less expensive FiiO IEMs are still great.
Please note I didn’t say anything about wireless earbuds for a reason. If that is what you need, that is what you need and there is really no reason for you to be reading this post. Just go do your own thing. I hope they make you happy.
[editing note: yes, I saw the typos and I believe they have all been corrected]