Of anything, I would choose my vintage Chanel Mini. She's a lambskin lovie from 1991 IIRC. I love my MonMono Neverfull MM but that can be easily re-bought. I've only had the mini for a couple years but I always wanted a vintage Chanel and she fell into my life at the right time .
My gold Hermes Birkin 35 - because it's my first (and so far, only!) Birkin, and was a first anniversary gift from my darling husband so it has lots of memories attached to it