Dressy: Accessorizing a simple black vest (Elizabeth and James, $395) and leggings (Riller & Fount, $101) with floral brooches (Moschino, $245 and $260) and a sparkly belt (Krizia, $485) makes this simple outfit chic and elegant. A low-heeled black boot (Johnston & Murphy, $328) means it's still easy on the feet.

Next: Effortless and easy