With day temperatures at surprising highs and nights dropping to predictable lows, layering is a must. For a brisk walk to their next destination, celebrities like Miranda Kerr are adding tights and hip editor’s jackets to their shorts-and-tee combinations. Alessandra Ambrosio bravely bares a taut midriff in a cropped, fur-trimmed sweater, while Rosie Huntington-Whiteley and Alexa Chung reveal naked legs beneath chic woolly skirts. When crisper weather calls for protection from the elements, fur toppers, wool trenches, and toasty parkas are in order, as demonstrated by Olivia Palermo, Liv Tyler, and Anja Rubik, respectively. In keeping with the season’s most popular pants silhouette, cropped skinny-leg trousers are a great way to balance top-heavy proportions. Opt for leather like Palermo and Ambrosio, slashed denim like Gisele Bundchen, or leopard-printed velvet like Kate Moss for additional style points. A selection of transitional wardrobe options awaits in our Street Chic gallery above.