I have a lambskin leather jacket that was purchased in Turkey by my wife's father over 20-25 years ago. After he passed away and she married me, my mother-in-law gave it to me.
I got my old Ramones t-shirt from the 80's - it's from their Road To Ruin Album. I want to keep it for ever so I only wear it once a year then hand wash it. I also got the buckle from my old peace belt that dates back to the early 70's. Cheers and happy weekend!
I kept a couple of shirts from my early triathlons -- also in the early 1980s. By the time I got around to wearing them again I was too far out of condition to fit into them. I must throw them out. :)
Not sure if it's the oldest but it is definitely the rattiest looking. I have a zip up sweatshirt that I wear ALL the time. It fits perfect and is not to long. It's not too thick and not to thin, it is just right. It is so worn out and the stains are permanent now. The cuffs look dirty even after a good washing. hahahaha but I lurve me ole sweatshirt. Sure wish I could find a new one just like it. I've looked but so far no luck.
I have a shirt that I bought at Dollar General in 2000. It still looks brand new and I wear it a lot. It feels like it's made out of t-shirt material. I think I paid $5.00 for it, I am sure it was under $10.00.