So I just gave away two big bags of clothing to Vietnam Veterans of America - they're awesome, and pick up at your house! - and I was disheartened to see it made no dent in my closet whatsoever.
As I was picking through my stuff, I came across a ribbed, brown velour mock turtleneck I bought at the Gap I believe around 1994. (Trust me, it looks better than it sounds.) I used to wear it all the time, but haven't in a while. I tried it on just to see if it even fit anymore and it did. And it's so slimming and comfy. I just didn't have the heart to give it away. Same with a dress I bought for $10 in New York City at one of those...$10 clothing stores.
I also have a pair of cherry red Doc Marten boots I proudly bought in 1993 when I lived in England. Except for a sweater from 1968 handed down to me by my mother (I call it the Picture of Dorian Gray Sweater, because it doesn't age) I think the boots are the oldest things I own that I still wear occasionally.
So, I'm curious, KFI fans - what's the oldest thing you own that you still wear?