Now is good time to be thinking about silhouettes. As we weather cools down (or warms up slightly, depending where in the globe you are) you have the option of committing to a slim, streamlined shape and relying on fabrics like merino and cashmere for warmth. Alternatively, you can start to play with texture and layers for more shape and volume - like a big jacket or wrap paired with bare legs. The examples in thisAllure editorial from 1993 are good because both silhouettes are accessible and complimentary.
Allure magazine September 1993 "High Contrast"
Lucie de la Falaise & Cecilia Chancellor by Mark Borthwick
Source: The Fashion Spot