What headphones should I buy for my iPhone?...

So a good friend of mine told me he just switched to an iPhone and that he wasn’t happy with the earbuds. Since I was going to get a bunch of links for him anyway, it’s a perfect excuse for a new sound roundup (see previous post here)! There are some new entries, and better yet new resources to check things out yourself. Between running, having an addiction to buying music, and producing Marketing Over Coffee I spend (waste) a lot of time worrying about audio. There are two hard rules I can guarantee you – one, there is no substitute for testing. There’s no universal fit, and only you can decide what sound quality/price trade off you can stomach. Two, yes, the stock earbuds stink. First is the fit category, I’ve cut into 4 options: Over the ear – These cover your ear completely and because they are so big this means you’ll get more bass than anything smaller On the ear – Slightly smaller, but personally I’ve found them more likely to hurt after prolonged use. Overall I ignore this category, if you have any you like in this segment I’d love to hear about them. In the ear – These are your standard earbud style. The key here is that they go in your ear but do not seal it shut like an earplug (that would be #4) In the ear canal – These have an airtight seal which has a tradeoff – they can sound much better than #3, but you can’t hear what’s going on around you as well. Some people don’t like cutting off the outside world, for example I prefer #3 for running so I still have some idea what’s going on around me. On the other...