My bags all fairly recent.
The oldest design of lens I currently have is my 50mm mk2 which ates from 1990, mine was only bought in the last few years. 2nd oldest design 100mm f2.0, then 70-200.
Of the earliest stuff, i've owned:
50mm mk1 (lost infinity focus and repair shop couldn't get parts)
50mm f2.5 (great on film, never rated on digital)
135mm f2.8 SF (very nice lens, would have breen brilliant 200mm equiv on my dslrs except for ancient afd focus)
70-210 f4 (owned two of these, good video lens btw)
100-300 f5.6 (not L) not great, in any way.
28mm f2.8 probably my favourite lens. Wish i'd never sold it.
And its great to see the 28-70 ii. Loved this lens on my 5 (a2e) 50e, 3, didn't make so much sense on my dslrs, and the filter thread was a masterpeice of poor design.