It's a Stretch

Honest opinions please: Does this work at all? I'm thinking about making the grey dress the top for the pleated skirt. Are the leopard flats all wrong? Am I trying to get too creative with the items in my suitcase?

Refresh:

Dress: Pure + Good Gertrude Ribbed Dress

Skirt: Tifus Dress Women's Pleated Velvet Midi Skirt

Necklace: Three Strand Pearl Necklace

Shoes: Sam Edelman Leopard Print Loafers