Outfit Details: Balakata Dress, Celine Bag (similar here, less expensive version here) Gabriela Hearst Sandals, Retrosuperfuture Sunglasses (sold out, similar here), Prada Headband 

Charleston always has a way of making September feel like an extension of summer, with long afternoons that stay golden well past the point the calendar has moved on. So I’ve got my eye on dresses that are light enough for August with sandals and a tote, but that will work just as well heading into the first days of fall, when it finally makes sense to keep a sweater over my shoulders.

I pulled together an edit of the easiest dresses under $300, all of them versatile enough to do both. They still let you soak up the last weeks of summer while catching that September ease, whether it’s a printed midi that works under a light jacket or a cotton dress I’ll wear with suede flats once I’m ready to ditch the sandals. These are the picks that will carry me from warm afternoons straight through to dinners that need a jacket.