My very first step down the downward spiral of headfi and really hi fi was the Klipsch Image S4i. I thought at the time for under $100 they were the best option. I've seen them on Amazon from $50-110 depending which version (ss411 or or more pricey enhanced base/noise canceling). Coming from stock Ipod earbuds and using the Klipsch I found for under $100 they were a dramatic improvement. There are probably others that can tell you where else to spend your $. I've seen some negative reviews on headfi-but I don't listen to them that much anymore preferring speakers.
I have Grado 225i that I pair with Schiit Asgard-2 with my dedicated components. I'm putting my resources into speakers and such. If I were saving a little coin for a "real" step up into headifidom with metal in mind as well as other forms of music and was willing to invest say under $1,000. Here's what I'd go for...this is assuming a first time purchase meaning you don't have HP, DAC/Amp etc. And, also assuming you're looking at dedicated listening to a PC set up or stereo rather than a portable rig.
Hifmian 500 ($700)-yes, it's some significant cash-but this will put you in the audiophile leagues with the big boys...like the popular Audeze LDC-2 that will run you over 1k.
Schiit Magni/Modi stack ($200) which will get you competent DAC/AMP. I heard this combo at a meet on this dude's laptop. For $900-that is a killer entry into serious hifi IMO.
Of course, there are tons of other options out there...more high end DAC/amps, but just looking at price point relative to quality-I think that's a really solid rig. Maybe all you'd ever need....
Edited by markm1 - 1/5/14 at 8:02am