I have a vintage Chanel flap bag that is very similar to the 2.55, I have a few DVF wrap dresses, and a Missoni scarf.
I have Loub heels but none of which I would consider classics like the Delic. I have funkier pairs.
I would LOVE LOVE LOVE a Birkin. I agree with the Burberry trench. The Lanvin Cocktail dress, yes, the D&G LBD yes, not sure about the others, but I would add:
1. Chanel pearls, or pearls in general
2. Dior sunglasses (vintage or new, kinda like a Jackie O style)
3. A classic fragrance (Chanel No5, or Thierry Mugler Angel, etc.)
4. A sexy pair of jeans.