I have quite a few things that I thrifted in the 90s that I still wear, and some of them were old (70s) when I got them. The black 70s leather jacket made in Uruguay with the envelope collar is probably my favorite buy ($7 from Harvard Square's Urban Outfitters basement when they included secondhand items, don't know if they still do). 1990 I think that was? Hmm...but I think the earliest purchased wearable I still have (as well as actually oldest item) might be my Victorian beaver top hat that I bought in 1980. It's really more costume wear now (as it always was), but I did wear it at a Halloween party in the last few years.
If we're talking about items that were actually new, it's probably the green Banana Republic leather flight-style jacket from 1988. A close second: the patterned, marble-dyed culottes I got at Pier One around 1990 that I have not worn since those years but will totally wear now. I am so impressed with their quality and comfort 25 years later.
ETA: Sneaking in a pic here from an outfit test session. Ancient rayon culottes with this-year Tencel chambray shirt from the Loft, last year's dark silver Birkis. Should work for a beach trip later this summer. (It's hard to see the colors here...culottes are pale blue with olivey-green marbling and black print.)
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