You never forget your first . . . music player! Seeing this Winamp t-Shirt ($18) really brings back my Napster-abusing memories.

I changed my Winamp skins monthly and relied on it as heavily as any app I love now. How young I was then — no glimmer of iTunes or iPhones yet to distract me. I'd rock this with glee — and couldn't wait for the knowing glances of passersby that will definitely be picking up what I'm putting down.