Get BOSE's in-ear headphones (pretty sure they only make one). They are $100ish and I bought mine about 5 years ago and they still work fine.
Longest I've ever owned headphones that I used semi-regularly. Usually one ear will stop working, but my BOSE are still going strong.
My favorite thing about them is that even if you are listening at a high volume, people around you cannot hear shit. Any other headphone I bought, I found this to be a problem when I was listening to music in a public place, like a bus or something.