I recently compared my Shure $150 SRHDJ head phones to my roomates $500 or so sennheiser hd 650s plugged into a $275 preamp and can honestly say the difference was hardly noticeable. I'm not an audio pro but I'm a musician with a good ear who has had a lot of kinds of headphones. For the money I can't justify sennheisers. Anything by Shure has been top quality, I've had a bunch of their stuff.
I like Bose stuff, except for the noise canceling headphones. It is not accurate. Most people don't know how to set up their speakers in the first place so a pair of excellent speakers in the wrong configuration will sound awful. Bose products sound pretty good under almost all circumstances, while requiring little or no expertise to set up. They're not for the sort of people who like Emacs.
Speakers (as in, small-mid-size near-field monitors, from very expensive to why-not cheap): Genelec ($3000), Adam ($2000), KRK ($750), Logitech ($100). Tastes in speakers vary a lot, and it makes a difference where you will be using them. These numbers are for the upper-middle end of the range. I like KRKs for their clear but slightly forward sound. I don't need a pair of Genelecs, but they are amazingly good. Some people swear by the Adams, they don't evoke any strong response from me. At the cheapie end the Logitech stuff strikes me as having a surprising level of bang for the buck, but it's been a while since I listened carefully to anything like that.
Buy powered speakers. Don't waste money on passive + amp combinations unless you have strong opinions on the electronics of different amplifier classes, in which case you probably want to build your own at some point.
Definitely. I've recommended them on HN before. They're the best 'pro' headphones at a very fair price that the companies making overpriced 'amateur professional' products don't want you to know about, including Sony themselves.
Offhand, only anecdotal. For much of the last decade, I have done production sound for film and video. I generally use Schoeps microphones, which cost a couple of thousand apiece (just so you know cost isn't a factor here). The reason I prefer MDR7506s is that when I'd set up every day, they're the only headphones that sound the same when I put them on as when I take them off.
The other responses are talking about headphones, but with regard to loudspeakers (and given that this is Hacker News) you can always pick out your own components and build your own loudspeakers. That will allow you to tailor the speakers to your specific sound quality and aesthetic requirements.
It helps to have access to decently-equipped wood shop, but if you don't you can try asking a local custom-cabinet maker if they will cut and assemble the box for you. IME they are receptive to these types of projects since they can often use scrap from their other projects which allows them to make some money from material that would typically be wasted.
Grado is not bad, but I don't think their goal is faithful reproduction of the sound either.
I own a pair of Grado phones, and a pair of Sennheiser, high end. There's a pretty big difference between the two.
The Sennheiser is, for lack of a better word, "transparent". It's like the sound is coming not from a pair of cans, but from "out there". It's very easy to forget you're wearing phones. It's like they don't have any personality of their own.
The Grado, OTOH, is very different. The sound is very much "in your face". Can you hear all sorts of tiny details and nuances? Sure, but that's because they were magnified a lot, to force them to become obvious. A look at the response curve tells you why: Grado likes to crank up the high-frequency response on their cans. They are great, though, if you're mixing audio tracks and are keeping an eye out for tiny mistakes.
The Sennheiser is like a wide-screen TV. The Grado is like a microscope. Both are useful, but for different purposes.