I don't have anything that interesting. Oldest stuff is most of a Craftsman tool set and toolbox my bride gave me the first or 2nd year of our marriage - wudda been ~1968.
Prolly the most interesting is something I acquired around 1972. I was a helicopter pilot in the USAF back then, and there was an unwritten rule that if you found any tool left in the cockpit by a mechanic, it was yours. I still have the duckbill pliers I found on the floor, and use them very frequently. And Duck himself liked them so much when working in my garage that he bought a pair for himself. They are unusual, but if you ever use a pair, you'll wish you'd gotten some long ago.