The oldest bit of tech I still use on a weekly basis is a Mastech digital multi-meter, bought from Maplin on a clearance deal circa 1982. Although I have much more expensive and accurate bench and hand held DMMs available, the old school segmented display on the Mastech is easier to read for basic V, I, R checks.
The laptop I keep in my tool bag is a Dell Latitude E6230, Gen 3 i5, circa 2011. Tough as old boots thanks to the mag-alloy frame, a keyboard that keeps up with my typing speed, and cheap enough not to worry about breaking it or losing it. I could quite easily convince myself I need to spend a grand on a new laptop but nothing on sale today comes even close to ticking the right boxes.
Around the house I have a Rega Planar 3 with AT10 cartridge from the early 1990s, a pair of Ruark Epilogues on the music system and a pair of Mission M7Ds surrounds on the TV system. My wife is by far the worse for clinging to old tech and still won't let go of our old Minidisc player.