Canon AE-1 35mm Camera, 1981. I just ran two rolls of film through it on the weekend.
I recently sold a camera from 1963 (I used it, not just a collectors item).
I have a camera from 1954, but I don't actually use it, so it doesn't count.
Viking Sewing machine, 1960s, not sure on exact year.
My drinking glasses and steak knives were wedding gifts to my parents, do those count?
I'm not really sure any of those really meet the OPs intent though, since film cameras, sewing machines, and steak knives aren't things people upgrade on the 3year/6month cycles lots of gadgets are now on.
My DSLR, which is definitely an upgrade-treadmill gadget, is from 2007 - although I expect to upgrade it this year or early next, so I don't think that counts either. So far I'm sucking at this game.
My phone is running Android 2.3, I think I got it in 2011.
My MP3 player is from the mid 2000s - it runs on a AA battery and takes SD cards. Okay, that one actually counts!