I've been enjoying my Sennheiser/Massdrop HD 6XX (= HD 650), which is powered quite amply by the headphone output on my Muzishare X7 integrated tube amp.
I don’t typically use headphones, but when I do my favorite pair is the Meze 99 Noir. I also like my pair of Sennheiser 6xx quite a bit. Both pairs are from Massdrop.
For the past 10 years it’s been the Sennheiser HD650. But I’m now at the stage of considering moving to the HD800s or a pair of Stax SR-oo7.
For desktop listening HD6xx w/JDS Labs Atom amp and Topping D10 amp For flights Bose QC 35 For walking the dog, going for runs, and falling asleep listening to podcasts Apple Airpod Pro When I worked in an office Shure SRH840 for closed back I have been listening to music almost exclusively on my stereo since being home for Covid and my HD-6XXs are basically relegated to conference call duty. If I could keep only one pair it would be the Airpods every time. The noise cancelling is great, as is transparency mode but I listen to 99% podcasts and audiobooks on them and any time I'm home I'd pick speakers. I've heard some very serious headphones and amplification and I'd still pick speakers every single time.
I've been a casual headphone listener for 50 plus years but now practically all my listening is done using headphones. It was investment like someone buying a new set of speakers or turntable. Definitely the last pair of cans I plan on ever buying. What's crazy is there are headphones sold that makes those look cheap.
For "serious" headphone listening it's my Stax SRS-7100 system (and jolly nice it is too!). I also have a nice pair of Audio Technica Grandioso ATH-W1000x near the main system if I just want to plug straight into the DAC (Marantz HD-DAC1) or integrated amp. For DAP I use either Sony WH-1000xm3 (wireless) or Final Sonorous VIII (wired) - the latter are complete overkill for that purpose but while in themselves they are great headphones they are only 16 ohm impedance so don't match easily.
Are there any DAPs that support itunes? I want to transfer my itunes library, but it seems like most DAPs don't support itunes.
I think in the real world you're stuck with either an iPhone or iPod Touch for using iTunes. Most of my files on the DAP I use most often (Cowon Plenue 1) are FLACs ripped from CD, or downloads from inserts with LPs. I'm sure there are ways to convert an iTunes library to 'play nice' with other players but that's beyond my knowledge I'm afraid.
For general listening I use the Grado SR-225. It’s light weight and sounds good enough. For serious audio bliss I have the Audeze LCD-XC but it’s heavy bulky and uncomfortable after an hour. For brick walled and other challenging recordings I use the Sennheisser HD-650; sounds good and no fatigue.