Where to buy: Sadly, fewer and fewer brick-and-mortar retailers carry quality headphones, and even fewer actually let you try the products in the store—especially if you're talking about in-ear-canal headphones. This makes it difficult to audition the sound and fit of headphones before you buy them. The solution, if you will, is to buy from a retailer with a generous return policy, so if you're unhappy with the way a set of headphones fits or sounds once you get it home, you can return it. This goes for both local and online retailers. For example, Internet headphone retailer HeadRoom carries a huge assortment of great headphones and offers a 30-day, no-questions-asked return guarantee—even on in-ear-canal models.
Headphone styles: There are literally thousands of headphone models out there, varying dramatically in style, audio quality, features, and price. But nearly all of them fall into one of several main types: earbuds, in-ear-canal, canalbuds, lightweight, full-size, noise-canceling, or wireless. Below are brief descriptions of each of these types, along with a few of my recommendations at various prices. I've noted which models include an Apple-style inline remote/microphone module. (Prices listed are MSRP; you can find many of these models at significantly lower prices.)
Earbuds, the type of headphones included with every iPod and iPhone, sit loosely in your outer ears. Although earbuds don't produce outstanding sound, they're compact and relatively inexpensive. Apple's stock 'buds are actually decent as earbuds go; you're not going to get a big upgrade in sound quality by simply replacing them with a different model. Still, there are a few alternatives out there that provide modest improvements if you're looking for a new set.
These headphones, also known as canalphones, use silicone or foam eartips that fit snugly—and fairly deep—in your ear canals. Like earplugs, they block most external noise, so they're great for travel and noisy environments. They're also capable of producing stunning audio quality. On the other hand, some people find canalphones to be uncomfortable, and the best ones come with an equally stunning price tag. (For more information, check out our primer on in-ear-canal headphones.)