The oldest piece of technology that I bought brand new and still have is my NES top-loader console I bought in the early 90s. Not sure that counts since I haven’t used it in years, since I downgraded to the original front loading model since the top-loader only has a coaxial output and the original has AV output.
I guess my Gameboy Advance SP I bought in 2004ish and still occasionally play is probably the oldest thing I personally bought and still use.