I'll buy maybe one or two new Coaches a year, mostly Duffles because of the size, but the older bags are still my favorites. The quality and softness of the leather is so much better than the current bags, and as far as I'm concerned most of those leather bags will never go out of style.
Mine go back as far as 25 years, from the old two-toned Spectators with the smooth leather through the Sheridans, Madisons, Sonomas, Willises (6 in different colors), Tafts, Court Bags, Station Bags, City Bags, a Fletcher or two, a Tribeca, a Bridle, and a smattering of the smaller "going out" bags.
I get more compliments on my Willises and my aubergine City Bag than I ever get on my newer ones. All it takes to keep them looking good is a very light wipe with Lexol Conditioner.