I have a last that was my grandfather's, and still use it to mend shoes occasionally. My grandfather was a foundryman, not a cobbler, but when he was out of work during the Great Depression he used to go and fetch sacks of shoes from the cobblers at the end of the street and mend them on the table at home. They had no money for things like bedlinen and often went hungry, but at least my father had a pair of shoes for school, unlike a lot of other kids who went in bare feet.A couple of Cobblers' lasts, now doorstops from about 1940 that dad had from setting up his cobblers workshop in the 1930s
My Dad still uses an early 70s Goblin teasmade.
Smock? Para?I've some spanners and tools that are pre war and get fairly regular use. I still wear my British Army DPM smock that was issued to me in 1987, essential dog walking wear.
Aside from that, the oldest thing that gets used a lot in chez Drago are my jokes.