I've never in my life seen a pair of headphones like the stax-sr202. Thought it was a joke till I looked them up.
They're ridiculous. The design is from the 70's, the technology is from a bit before that, and they creak with every move. The build quality is terrible. They're absolutely unlike anything Apple has ever made. But they make up for it by having one of Apple's core values - they're insanely great. They sound like nothing else in the world and they give me a benchmark to apply to anything else - even with the lacking low-frequency response.
The SR-009:
This is their flagship. Gorgeous aluminium, amazing build quality and nice leather pads. But they're also $5600+- excluding the required amplifier (which, if you're buying that thing, should cost about the same to get the same reference class quality). This is the pair of headphones that $100k speaker rigs should look up to. From the reports, they are the most detailed things ever made. Steve would have loved and hated them.
Anyway, back on topic:
Another, kind of crazy option, is the custom in ear monitor market. Per example, Fidelity:
http://www.fidelitycustomearphones.net/products-page/earphones/fidelity-duals/
They're all-custom, bespoke made-for-you earphones. I've owned a pair of Ultimate Ears UE-11's for a few years. For portable use, they might be the best sound you can possibly get. But the UE-11's are over a thousand dollars, and the Fidelity is the same idea brought to 260-ish dollars.
They can have a lot of different looks, although they will always look a little like hearing aids. Mine look like this:
http://dl.dropbox.com/u/11612892/IMG_0126.JPG
http://dl.dropbox.com/u/11612892/IMG_0127.JPG
They contain four drivers each. The cable is replaceable. And that goes for the Fidelity earphones I mentioned as well, which is closer to the OP's price.
It's something unique

.