Grado - SR80x

I'm with you on the comfort and EQ actually. I can wear my 900s for hours, they are extremely comfortable. It's amazing what a difference a little adjustments to the EQ can do. I bought a pair of Audio-Technica m50x-BT2 for on the go. They have a parametric EQ. I asked ChatGPT to give me settings for it that would make them sound like my Grados but with bass. They don't sound exact, but they sound good. As far as my actual Grado SR80x goes, I bought the sheepskin pads for them which really brought out the bass, but I lost that musicality they are known for, so again, EQ saved them. Now I have extremely comfortable Grados with bass. Again, not sure if I'll reach an end game per say (I like the way you frame it though), all I know is I'm having fun and that's what matters.

At home on my laptop it's DT 770 Pro, 900 Pro X and Grado SR80x through the Zen DAC V3. Out and about it's Sony ULT Wear or JBL 770NC. I like all of my headphones for different use cases.

Of the eix main pairs of headphones that I use, three are wired and three are BT (all three of them can be wired though). I'm at home most of the time so my daily drivers are my Beyerdynamic DT900 Pro x and 770 Pro 80 ohm. I have a pair of Grado sr80x that I also enjoy from time to time. For wireless on-the-go use cases I usually use my AT M50xBT2. I also have the ULT Wear and JBL Live 770NC. My ears aren't trained well enough to notice a difference from BT, but my BT cans are all consumer grade, that's what makes the difference.

Yes kph 40, you can easily change earpads if desired. Very good sound and featherweight. Under $40. Portapro and kph 30i too. Kph 30 wireless if you don't like wired. For much better sound and a step up in quality: Grado 80x and Sennheiser 560s. Comfortable and light but not like the Koss.

Grados are sharp. I adore mine, but you should know they are not for everyone. I highly recommend you start with something cheap and neutral like the koss kph40 or the new Moondrop Old Fashioned. Both are excellent headphones and are just about the comfiest thing you can get. Otherwise if you can spend a little more than your budget you can get Hifiman Sundaras - they are still some of my absolute favourites despite having headphones that cost twice as much (back when I got them in 2021 they were 300$ now you can find them for 140$). If you’d like something closed-back fiio Ft1 are my best recommendation, but again they might be a little over your budget.

I've got a pair of Grado SR80x and it's almost like having nothing on my head at all. The THICCCCCC cable on the other hand

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.

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

You didn't mention a price range, but if PortaPros are your benchmark I'm assuming you're not looking to spend a ton of money. I would recommend the Grado SR80. They sound fantastic, are built pretty solid, and cost about a hundred bucks or so.

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.