Why: "Clothes that follow the shape of the body, without clinging, are the key silhouette for fall," Greenfield says.
What to look for: An original shape to the jacket — pronounced lapels, a cinched waist — and precise, well-cut tailoring.
What’s modern: Pairing a strong suit in a subdued color, like gray, with a silk shirt in either a bold color or a soft print.
Pictured: Ports 1961 by Tia Cibani wool blazer, $550, and pants, $550; special order, 866-433-7678. Ports 1961 silk top, $785; Nordstrom, 888-282-6060.