Layering is key for the cooler months. Pile on a chunky long cardigan or an edgy fitted leather jacket atop skirts, pants and dresses. A great tailored blazer is another great layering option, and works from day to night. Wear a jacket over a cardigan over a frilly blouse, for instance, and make sure each under-layer peaks through in the name of style.
Pictured: Antonio Melani Giovanna Jacket ($499 at Dillards.com)