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, $995) 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, $23) with open-toe shoes from summer (Halston).
Cuff, Ewa Solarska.

October: The dress acts like a skirt under a long pullover (Tibi, $340), accented with a belt (Linea Pelle Collection, $225), and python ankle boots (Fratelli Rossetti).
Earrings, Ted Muehling. Brooch, Fabrice. Tights, Wolford.

November: Now you need a real coat (Charles Nolan, $998), knee-high boots (Michel Perry), a scarf (Yarnz, $168), and gloves (Burberry).
Belt, Linea Pelle Collection. Tights, Wolford.
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