“The most important thing for fall is a nice coat—a cool trench, peacoat, overcoat, or leather jacket,”explains Legend, whose fifth album—along with a new music talk show he’ll host on Showtime—is expected in early 2012. “In New York, [the coat is]what people see first. Burberry is always good for a classic trench. That’s what they do. I also have a really nice Rag & Bone overcoat that I wear a lot.” Designers such as Billy Reid (shoes), Alexander McQueen (anything), Prada and Gucci (suits), and Audemars Piguet (watches) round out Legend’s list of favorites.

But a fly pair of slacks and some ill five-inch heels—that’s what he likes to see Estelle rock…