A pair of Gucci lug sole horsebit loafers that I bought back in the 90's. I've worn them hard, still wear them and they're in great condition! They were $295 back then, they're going for $1150.00 now.
A pair of brown and black Chanel Spectators I got in the early 80's from the Chanel boutique in San Francisco. Funny enough Winona Ryder and Johnny Depp were in the store shopping at the time I was buying these. It was all very exciting and felt so glamorous. I only wish I could get my mommy feet back into these beauties today!
I have Manolos sandals which are worn to death but I can’t let them go. Maybe 15 years old?
My mom though has some pairs of Dior stilettos maybe 45-50 years old?