I actually have a few answers to this. I have a Sweater of my dad's from when he was in college - it's the most ridiculous thing ever, and I actually can't imagine him wearing it. My prom dress was from the 30's, I think (we researched it when I picked it up at a yard sale for $3, and it turned out to be worth a ridiculous amount of money online). The oldest thing of my own that I both own and frequently wear is actually three pairs of blue jeans that I got when I was in 8th grade. They were the only things that I could find that fit me well and cost my parents almost $50 each, which was a huge deal at the time, but they can't say that I didn't make them last!