1997 grad here. My senior year I bought a pair of black Doc boots and wore them throughout college. Mine, like yours, have disappeared. Maybe they're kicking it together somewhere.Apparently, I'm roughly @wasmisterfu age. Graduated HS in 1994 and in those heady days I owned only 4 pairs of shoes. Birkenstocks, black shit kicker steel toe work boots of unknown origin, grotesque black disposable dress shoe abominations, and sneakers.
Incidentally, I also had a pair of Docs in 9th grade. As I recall, they weren't a super fit and were minimally worn. I searched high and low through my parents' house last year for that pair of boots prior to the house being sold. Gone! No idea what happened to them. I can only guess that they suffered the same fate as that of my Dad's baseball card collection in the 50s.