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@Chris.
Sennheiser PX 100.
Over-the-top style headphones, great quality sound, good bass, fold-up, and can be had off eBay for about £25. Use them with a clip-on iPod Shuffle - great combo for cycling, and if either of them happen to get broken, it's not the end of the world (luckily hasn't happened to me yet).
Regarding cycling with music in a city... I do it in London. May be slightly safer without listening to music, but then listening to something you like is much better than honking horns and angry pedestrians/drivers. Also makes me cycle faster and harder. I guess it comes down to if you trust your vision as much as your hearing.