If you like blue jeans and have a spare $250, you might want to pick up a pair of Levi Redwire (TM) jeans. They have a built in docking cradle for iPods that lets you pull the iPod out of a special pocket while it is playing. Why a cradle? The jeans also have an integrated iPod controller that sits outside the pocket, so that you can have your iPod safely tucking inside the pants but still access the controls. It also comes with a retractable headphone unit to help keep your headphone cord from becoming tangled.
Presumably all of the electronics in these pants are removable so that you can wash them. And these pants will likely spur a thousand variants of the very old joke, "Is that an iPod in your pocket or are you just glad to see me?"