Forever stay Fly. Relevant.
For music its whenever you hear it, it be album or song, you listen. Not because it reminds you of of a particular time, its because you dont want to miss it, afraid it might be the last time you hear it. And that will suck. There are few albums that can claim the title of a classic. Fifteeen, maybe twenty. Some you have slept on. Only Built For Cuban Linx, anyone?
Ever heard a song on the radio, and you crank it up even though you have the cd right there?!
As for gear, its the fact that you can still rock it today the same way, same way, you did in 1984. The Wheat Nubuck Timbs. All White AF1. Adidad Tracks.

Yo I'm tryin to make a dollar out of what makes sense
Add it up, told my daddy I'd be a rich man