I've been quite lucky, first off I find a pair of Bose earbud things for £25, still using them, awesome quality, comfortable, great noise reduction etc. Best 25 bucks I ever spent. I use these things every single day, and I've gone through dozens of pairs before I got them, typically it would be a full on break, or a broken wire, and I'm shopping again, but as I said I been lucky.
And secondly, my Sennheiser headphones are still going strong and sound awesome. I think they cost £40, and I'd choose them over any skullcandy/dre/gaga/douche&co headphones on the market. Those 50cent headphones are aparantly pretty good, but I wouldn't pay the asking price for those. I like my headphones to encapsulate my whole ear, there's nothing worse than tight headphones that dig into the ear cartilage, go big or go home, that's my motto

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Really, I think it's better to find a good manufacturer, something that will be good, and will last, rather than going for the equivalent budget option. I'd rather have pre-owned than cheap. Apart from the ones I have now, I completely agree - seems the more I spent on earphones the shorter their lifespan... especially the wires breaking... cheap earphones crack open like acorns, and expensive ones end up with broken wires. Of course, sometimes it's my fault - I have killed a few pairs by them falling out of my ear, and into my coffee.