Hmmm... oldest that I still wear once in a blue moon is a Florida Panthers hockey jersey from '93 signed by Martin Straka and Radek Dvorak.

Oldest hanging in the closet are a couple of Karate and Ninjutsu gi's from '86-'91 that I keep around in the false hope that eventually I'll get back into shape again... someday...

Oldest that I have packed away somewhere is a denim jacket from '83 that has a hand painted design of a black heart and sword with Loyal Rogues in calligraphy. (The birth of my handle and renaissance group.)