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So they'll leak in too much noise?...
Well screw it, I can deal with that using my Shure SE215s.
I really wanna go HD.
Maybe an HD598... and a Fiio amp?
Or should I go on-the-ear V Moda M-80 and Senn's HD-25?
Depends how you want to use it... if you want truly great sounding headphones, you should look at non-portable ones.
HD598 - coming from the M50, you'll notice a huge soundstage, with far superior midrange - vocals. I still haven't heard a phone that beats it in the midrange aspect. Love the treble and soundstage of this can. Bass may disappoint you. Smooth signature (like with all Senn) may be a turn-off if you're not used to it. Comfort is fantastic.
Q701 - virtually a HD 598 that is more amp dependent... and I consider it to be inferior.
D2000 - sounds a lot like the m50, but better. Less of a recessed midrange, though it's still pretty recessed, but far better bass and treble performance. Soundstage is far bigger and deeper than the M50's. It's a "closed" design but it's actually more open. Awful noise isolation. Treble was fatiguing. Comfort is fantastic.
HD600 - hard to find for a good price but the most neutral dynamic driver can. A bit small in soundstage for an open back to be honest. Good midrange performance.
HD650 - better soundstage than the HD600 but it's more expensive, very amp dependent (voltage wise), worse bass imo (texture and quantity), treble a little too rolled off imo, very relaxing. Good midrange although bass often takes the spotlight inappropriately.
HE-400 - very popular can these days. I never actually heard this one but they are better than the D2000 from review comparisons I've been reading
DT 880/ 600 - sort of suffers from the same problems (recessed midrange/ harsh treble) as many other high class cans but very nice airy sound, great imaging. Slightly more bass than the HD598 or the Q701. Comfort is fantastic.
DT 990/ 600 - never owned one but apparently really nice soundstage, a bit notorious for V- shaped sound. Comfort is fantastic.