Grado - SR80 (original)

For sure! Enjoy those grados though I had the sr80 og and thought they were very fun. If you’re finding them uncomfortable you can always try a comfort strap from Capra audio. I’ve had them on basically everything

The Grado SR80 were the pair for me that really opened my ears.

226s would be overkill. The SR80 series is a great set of headphones.

Grado SR series. They're open-back. You can hear everything.

New? Ft1 pro, the regular Ft1 is good but not "big ass easy to drive planar magnetic that come with both 3.5 and 4.4 cables. For about 200 But year on year, used grado sr60, 80, 125, and 225's. Used pristine 125e's are like 50 bucks everywhere and they're just a fabulous set of cans, and durable as hell.. But new, its the Ft1 pro, no contest. Or iems. Moondrop kadenz are just astonishing for 200 bucks. But the simgot em6l are also amazing for 100.

I have yet to find anything better than my slightly modded Grado S80's :-)

I currently use a 30+ year old pair of open back wired Grado Labs SR 80 headphones to stream classical music on Apple Music and Spotify from my IPhone 16 pro through a portable DAC amplifier connected to the headphones. The headphones are still in great condition and sound much better with lossless music than my Bose sound canceling ones or IPod second generation pros. However I wonder if I could get significantly better lossless sound with more expensive wired headphones of no more than $250 or should I stand pat? I could probably find recommendations from Consumer Reports or the NY Times Wirecutter. However I have been impressed by the number of knowledgeable audiophiles on this subreddit channel. Could some of you give me some recommendations with reasons for those choices? I suspect that my question has been answered before on Reddit. If it has been answered recently I apologize and request that someone provide me with a link to that question and responses. Thank you.

Yes! I usually only play with headphones in the $200 and under range. I actually don't remember when I last paid more than $100 for a pair recently. I pretty much like anything from koss, I haven't tried the porta pros or kph-40 yet. The kph-30 and ktx-pros are good but the ksc-75 are still my favorite. ktx-pros are a little more warm and basey very similar to the kph-30. I never had a pair of mdr-7506 but I still have a pair of V6, but I don't know if you can still buy them. They're great for pop. I also tried some used Grado sr80s and I didn't like them as much as I'd hoped. They sounded really bland, like little to no base and midrange. Still like grado as a company and think they're worth trying again especially if I find a demo setup. I want to save up for some berrdynamic dt-770 or dt-990. I remember trying them in microcenter once and loving the sound.

If you're looking for decent wireless noise cancelling in that price category you can always grab a pair of Soundcore Q30 (or 35 if you can get them used/on sale) For plain old wired headphones in the $30-40 range you can always snag the Koss Porta Pros, or the KPH30i. They sound much better than you'd expect, especially if you swap out the pads. Moving up the price range you'll find things like the Audio Technica ATH-M50x (Wired or Wireless), Grado SR60/80 (Wired), Beyer Dynamics DT770 (Wired). These all sound different, ATH being more bass, Grado lots of Treble, and Beyers are flat. If you like thumpy headphones you can absolutely enjoy Skullcandy Crushers, or Marley over ears. The latter have a pretty solid build quality whereas the other are more affordable. Everyone has a preference, so just enjoy what sounds good to you. I would probably shy away from unreviewed no name headphones like those you linked, though!

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.