The oldest LVs (I think!) in my collection are an Amazone crossbody and a zipped key holder, both in Monogram, both from 1995 and both in fabulous condition. The oldest one I bought myself is my Brooklyn PM in DE which I purchased in 2010.
I bought the speedy b 30 when it first came out, maybe 2012? Although red canvas is peeking through the bottom corners from using it and had to get zipper replaced, everything else is still in good. : )