Good question! I live in a warm climate, so I start wearing my navy canvas Sperry topsiders in February. For something with a little more polish that will take you all the way through to summer, I like a neutral ballet flat with a hint of flash, maybe a bow or a buckle.
These Cole Haan’s from Zappo’s are adorable, but you can find something similar at any price point:
I’m always happy to answer questions if anyone has a prep puzzle to solve.