1. Choose a soft material in a silhouette that isn't too extreme, so the look is more modern, less Mad Men.
2. Whatever you wear below the pouf should be streamlined: a pencil skirt or tapered pants.
3. Accessories should contrast with the ladylike vibe—choose an edgy metallic clutch or a bright stiletto.
Dress, Dressbarn Collection, $56, dressbarn.com.