What do you consider "good sound quality" with headphones?
For me, I think good sound quality is when your headphones can accurately represent what the musician originally intended for their song to sound. This is tough to determine unless you have the opportunity to sit in the studio with that person and hear it from the source.
If I can't get that, I usually like headphones that have a nice balance across all the frequencies. It's nice to listen to the difference between my $5 travel ear buds (gdgt.com/sennheiser/mx-400/) and my $100 over-ear headphones (gdgt.com/sennheiser/hd-280-pro/). You hear a lot more detail with the latter.
What do you look for when you shop for your "good sound quality" headphones?
Depending on the genre of music that can be challenging. The "top 100" music doesn't require much besides a little treble/mid and lots of bass so these cheesy headphones by Dr. Dre tend to suit the average listener pretty well (while abusing the hell out of their wallets).
I expect more and would rather have control over the level of bass, etc, via an EQ (which is a requirement for any music output device I'm going to spend money on).
I can accept the lower quality headphones for general usage... especially if I'm listening to streaming music but if I'm going to be listening for a long period of time I prefer to use my Etymotics.
The benefit of accurate drivers is that you do not need to turn the music up as much to actually hear the various ranges of sound and so they are actually not nearly as hard on your ears. I don't know how people can tolerate the distortion and loss of detail caused by the lower quality headphones/speaker set ups.
Anyway, in terms of choosing headphones... I research the range frequency, I look at what other audiophiles have to say about them, the intended usage by the company (sometimes they are focused on specific genres or whatever), and I test them... I usually start by throwing in some Mozart and end it by throwing in something electronic and demanding. It's a given that rock, etc, is going to sound fine on just about anything so I completely avoid that sort of music while testing.
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Everybody's tastes are different, and if you're not spending *a lot* of money on headphones, you're not going to get an accurate representation of what the sound engineers intended. The next best thing is to find something that *you* like.
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When I first set up those new speakers, I tested them with Mike Oldfield, Marc Cohn, and Sarah Mclachlan. I noticed details in the music I had never noticed before. I ended up sitting there for several hours going through our collection and enjoying many of my favorites as if for the first time. It was like a revelation... and it made me commit that day to never buying cheap speakers for our music again.
If you are looking for good headphones for the first time, you should have a similar experience. If not, they probably aren't very good headphones.
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What do I look for? It’s not just about the sound quality – it’s got to be ergonomically sound for me, and also conform to the particular role. e.g. there's no point for me having a portable phone if it doesn't have, at the very least, adequate isolation - the main reason why for example I ended up dumping the Ultrasone Edition 8's ( gdgt.com/ultrasone/edition-8/ ) as my primary portable phones. So given those attributes, I pick the least worst compromise based on a combination of all of those.
In terms of the specific sound I look for, I tend to gravitate to a resolving but laid-back character: A slight bass hump, recessed yet still informative trebles. One example of a headphone I keep coming back to would be the Sennheiser HD650 ( gdgt.com/sennheiser/hd-650/ ), as well as the sadly-underused Sennheiser Orpheus ( gdgt.com/sennheiser/orpheus/ ), which has the best-judged (for me) sonic character that I've ever come across in a headphone to date.
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Obviously, headphones that sound excessively tiny or bassy are not perfect for everything but as you've said, it really depends on how the musician intended for it to sound. You should, however, be able to hear everything that is going on in the recording. By this I mean all the details including instrumentals and vocals.
Personally, clarity is one of the largest factors in headphone quality but a good amount of bass makes everything sound better.
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For music listeners, it probably matters what genres you listen to most; almost all popular contemporary music gets compressed and EQ'd to target common playing devices: iPod earbuds and cheap radios. For this kind of stuff, you want to consider a quality set of "hi-fi" headphones that do things like bass boost and are targeted for active everyday listening. (This is the realm of stuff like Skullcandy, Bose, Beats by Dre, etc.. Audiophiles will knock this stuff, but are holding it to a completely different standard.)
If you listen to niches that value quality sound reproduction more – Classical, Jazz, Progressive Rock, that kind of stuff – then you want to go more the "studio" route, emphasizing headphones that prioritize an "uncolored" even frequency response, larger drivers, and perhaps isolation from ambient noise. The highest quality is going to come from bulky over-the-ear models, though you can also find a lot of high-end earbuds that target this same area.
Oh, and if you're doing any kind of production work, you should be minimizing your headphone use whenever you're touching a mix, equalization, or mastering. You need studio monitor speakers, and big ones at that.
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