Lauren Hutton in Ralph Lauren Black Label, The Row and Helmut Lang

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Night and Day
Changing for evening used to be a big production: The whole point was to transform yourself. But Hutton never favored frilly ball gowns that didn't feel like her. She pioneered the modern concept of glamorous elements treated in a more offhand way. The splendid sweep of this long, silvery skirt (Ralph Lauren Black Label, $1,098) teams with a fitted leather jacket (Helmut Lang, $1,325), layered scoopneck tees (The Row, $300 each), and Elsa Peretti for Tiffany & Co.'s Diamonds by the Yard necklace—a classic example of dressing down something precious. Ring, Patricia von Musulin. Shoes, Robert Clergerie.