By a strictly technical interpretation, a "better" headphone should have a more linear frequency response (after accounting for the HRTF) with as fast a decay as possible, in order to present the sound as accurately as possible. That said, accurate and pleasing are not necessarily the same thing. As I mentioned in an earlier post, a technically flat response will feel a little light in the bass and a bit weak in the treble/detail due to lack of room acoustics and bass pressures. Boosting these responses slightly in a headphone will restore that sense, at least artificially. You can also compensate for the acoustics via programs like Isone Pro, or Focusrite VRM. Some amps do offer crossfade, but this is a poor man's version of proper HRTF.
I've owned a myriad of headphones from the budget range, to the $100-200 range, and currently have an HE-6. There was a palpable jump from cheapies to some decent budget headphones, another smaller jump into the mid-fi range, and it took a big jump into the $1k range for me to get a definite "yes, these are better" feeling. Worth the price jump? At my current income level, no. I will be selling the HE-6 soon and am considering trying the HE-500 or just sticking with what I have. If I had more disposable income though... very tempting. Heck, it's very tempting to keep it even now, but gotta pay the bills y'know.
I've also done the climb with amps and dacs, having built my own cmoys and various other things, and owning dacs/amps from the $20 FiiO e5 to the $1.1k Nuforce DAC-100. Again, a noticeable difference, but serious diminishing returns, even faster than the headphones. Discernable jump going from a laptop headphone output to the iBasso D10. Moving up to the Nuforce, I have to really put my ears to the test to hear the difference unless I'm using difficult to drive cans, though in that case it's a matter of needing an amp that simple has better gain structure than the D10.
People tend to say source first in audiophile circles, but honestly the source feels the effects of diminishing returns fastest. I'm going to try and stick to a 1:2:3 rule for myself, which should be the relative value of the dac/amp/headphone (maybe more like a 1:1:2:3:5 rule, for cables
ower:dac:amp:headphone).
As for how to evaluate, just load up some of your favourite and most familiar songs on an mp3 player or bring a cd with you. Any dedicated shop should have a quiet listening room. Here are some things I listen for:
- cymbals - how they shine when struck, and not overbearing or shrieking
- drums - driving rhythm with a thump that doesn't overwhelm
- a solo voice in a room with good acoustics - listen for breath (literally)
- a group of voices - how well can you distinguish voices from each other
- acoustic and vocal - how well the voice is distinguished from the instrument
- piano - this is extremely difficult to reproduce clearly across the spectrum
- electronica with a treble line over a heavy bass line - just for simple separation