Low wedges and a comfy dress make for a laid back but still dressy date-night look. Add a scarf if it's cool. Not sure what bag I'd go for--probably something soft, worn, and boho.

Something with some pop to wear for lunch and drinks on a casual patio somewhere...a sweater in case it's cool or breezy and a pop of red--contrasted with the creamy enamel disc and sweater. Grounded with the bright, artsy-almost ethnic-wedges and a practical carry-all and jean shorts.