When your standard issue earbud monitors become uncomfortable or when you'e not getting the sound quality you want it may be time to upgrade to custom monitors. Most commonly seen on rockers and newscasters and now readily available to the rest of us, custom monitors are cast from molds taken of your ears—something quickly, easily and painlessly done in about 20 minutes at any audiologist for around $50 to $75. I researched several manufacturers and settled on Ultimate Ears, who offer a range of monitors that are highly customizable.
Unlike most earbud or over the ear monitors, you can't easily try custom monitors, so I had to rely on what I heard/read about them. I chose the UE-5c, which are made specifically for use with digital music players and computers. Rocker fantasies aside many of the other models seemed to be more than I needed, and cost more than I wanted to spend. I thought the clear ones looked best, though green was a close second. They come in a wide range of colors and skintones (which look kinda creepy unless you're on stage) and you can select the length and color of the cord.
In addition to the great sound quality and comfortable fit, another benefit of these custom monitors is that they create a seal in your ear, providing near total sound isolation from bad music playing in the gym, loud co-workers and ambient noise from airplanes, trains and subways.
They come in an elaborate metal box that is way too big (and too ugly) to carry around, but does make them seem like precious cargo. The monitors take some getting used to as they twist in and out of your ear, and during a lull you can hear yourself breathe. They are really comfortable, and I've been impressed with the sound quality, listening to everything from Beck to Madonna to Soel. Custom headsets are an investment, and if you frequently lose yours probably not a good idea. But if how you experience your music is as important as what you listen to, then $550 becomes oddly justifiable.