Usually but it depends on a few variables and it's not always worth it.
Because you're not used to it, high end equipment doesn't sound amazing in comparison at first - just oddly different. (At least not in a $400 to $100 comparison - the biggest difference is going from $10 to $100.) Once you're acclimatized, though, it's really hard to go back until your hearing naturally degrades and you're stuck buying high end gear.
So the rational approach is to never buy high end headphones or earphones at all and instead aim for the highest quality stuff under around $150. It'll get you 90% of the way there and stop you becoming an audio freak chasing an expensive pipedream. Almost no-one will give this advice, though, since audiophiles want to rationalize their purchases and reviewers or stores want you to buy their crap.
Definitely agree with going from $10 to $100. I bought a pair of Grado SR60 headphones a few years ago for ~$65, and they were by far the best headphones I have ever owned. I heard things on CDs that I never noticed before.
Strong agree on the performance curve for earbuds too. If you can buy it at Best Buy for under $100, your money is probably better spent with something nicer online.
In high-end speakers (hi-fi, whatever you want to call it) there are always sleeper brands that even the audiophiles will say offer an 80% experience for under 50% of the price... I remember (before several buyouts) NHT bookcase speakers being one of those. It's probably the same in headphones.
Please, for the love of God, take my word for this: it's also very much true of cars.
Grado SR60/SR80 are extremely cheaply built, mine had plastic pieces come off and one of the ear pieces sometimes snaps off from the head band. Really unacceptable. On top of that low frequency response is less than ideal. Old similarly priced Panasonics that I use as heavily are still in one piece and work reliably.
I'm using Sennheisers now, I'm not sure how it's going to hold on in long term, but for now it seems that they have higher build quality than Grados.
There's no gospel. Get what you think sounds nice.(1)
Go to a real hifi shop, where they actually demo the stuff for you in living room-like conditions (carpet, not warehouse ceiling etc., and no 25 TVs blaring MTV across the aisle), and listen to the difference between, say, $80 speakers and $500 ones, then try to figure out where your ability to hear the difference levels off, and get something in that range.
Bring a CD of the kind of music you enjoy. "Thunderstruck" is wonderful for demoing bass, but if you're into indie-fragile-weeping-dude, it's not what you want to base your purchase decision on.
If a place won't let your switch between different speaker/amp combinations on your time using your own music, you're not buying from them.
(1: Except one thing: cables. Don't get the biodynamic green tea infused ripoff stuff, but the ones that come with your stereo (even good ones) are most likely absolutely hideous. If you already have a setup, and use bad cables, spending a bit of money on decent cables is the best investment you can do.)
The only thing to look for in digital cables is build quality, so that the cables last, don't break, and you get your money's worth. I've got these quality ethernet cables I bought 15 years ago that I still use. They don't have to be expensive either. Pretty much anything you get from monoprice.com fits the bill.
I was referring to analog cables.. but yeah, if you're buying new, getting an end-to-end digital setup is entirely feasible. Still, you probably want a single minijack-to-phono for plugging in an iPod.
I've experimented with earphones from £5's worth all the way up to £230 odd for Ultimate Ears 10vi triple fi pros (I've also tried Shure SE530's and feel the triple fi's beat 'em).
The difference between the triple fi's and basically any other earphone is actually pretty astounding. The main difference is clarity; though it's a cliche, it really is a case of hearing individual instruments, etc. (though you need high bitrate for this obviously).
It is, however, an extremely expensive hobby (and you can't go back). Another great thing about the triple fi's is that you can replace the cable. Since the cable is usually the failure point of any set of earphones this actually makes it quite economical compared to, say, £50 earphones you need to replace far more often.
I had a pair of Shures that I paid over $200 for. Every other earbud I've tried has been terrible. They're tinny, they don't fit right, and you have to blast them to get over moderate ambient noise. I worked in a fairly noisy office when I had the Shures, and I could turn the music down to one click over 0 and still hear nothing but music. The sound quality was also a lot better than just about anything else I've used (save for my $290 pair of over-ear headphones). I ended up losing them (or they were stolen, not sure) and just never replaced them. I mostly work from home now, and no one here is going to care if I turn up the speakers connected to my desktop.
Were they $300 better, or even $50 or $100 better? That depends on what your priorities are. Me, I've spent a lot of time and money collecting a high-quality music library, and I prefer to hear it through headphones that are transparent and don't lose detail. Your priorities might be completely different.
I've spent roughly half that on single pairs of Shure headphones, and while I like the sound quality, I recommend avoiding them, because the cables are of very low quality. Jason probably doesn't wear his headphones out in the Chicago winters, but I do, and every pair of Shure's I've bought (I think I'm up to 4) has ended up with frayed cables or cable/driver connections.
Shure has an amazing replacement policy (it's basically no-questions-asked) and I like the company and the user experience, but losing a pair of $200 headphones every 6-9 months isn't acceptable.
I've been using the Ultimate Buds (what a terrible name [for headphones]) versions of FutureSonics FS-1's and Etymotics; in both cases, UB swaps out the OEM cable with Apple's vastly superior version, which has the added benefit of working as a handsfree with my iPhone. I highly recommend these.
It's not hard to see why Shure's high-end pairs are of higher quality than the low-end pairs; the 530's have more drivers than the 115's.
I live in California and had the same fraying cable problem with three pairs of Shures, so it's not the cold winters that cause it. As amazing as their sound quality and replacement policy are, I gave up and switched to a Chinese knockoff that had good reviews.
Depends. I can't hear the difference between $100 and $400 headphones in most cases. I have a $99 pair of Apple in-ear headphones and they work great.
I like to keep my music library fairly small, so everything's encoded at 160 or 192kbps mp3. Fancy headphones only help if you're encoding much higher or using FLAC/ALAC.
I am not sure about this specific model, but a lot of the high end ones are custom molded to fit your ear canal. It's a luxury, obviously, but if you are using them a lot and you can afford it, I think it's worth it. The ones I have double quite well as earplugs when I don't listen to music, and work far better than any specifically designed noise canceling headphones I've tried.
Ultimate Ears (now a subsidiary of Logitech) is pretty well known for their custom in-ear monitors. Prices go as low as $399, not ludicrously expensive. I've never used them personally, but others seem to be pretty well chuffed by them.
If you're over 35 don't bother, your ears will have deteriorated too much due to aging. Under that it might be worth it, the younger you are the better your ears. Try them before you buy them, and try a bunch of them in different price ranges it's not pocket change.
You can grab those shures for just above $200 on eBay. I got them but if I could go back in time I would have gotten something cheaper, or a headphone instead.
