Adam: "All those seasonal rules are over, ladies. Changing weather patterns mean fashion is now about adapting your wardrobe to wear year-round, not buying tons of new things. Layering is the key, but don't attempt it with something too tropical and bare; a fairly classic dress in rich, quiet colors (our pick: Marc Jacobs) is way more flexible. Add-ons should share the same palette."
September: Entertainment television host Chantal Bolivar, who is in her 30s, can save money by wearing cable-knit tights (DKNY) with open-toe shoes from summer (Halston).
Cuff, Ewa Solarska.
October: The dress acts like a skirt under a long pullover (Tibi), accented with a belt (Linea Pelle Collection), and python ankle boots (Fratelli Rossetti).
Earrings, Ted Muehling. Brooch, Fabrice. Tights, Wolford.
November: Now you need a real coat (Charles Nolan), knee-high boots (Michel Perry), a scarf (Yarnz), and gloves (Burberry).
Belt, Linea Pelle Collection. Tights, Wolford.