Lauren Hutton in Norma Kamali

In the Red
Clear colors and easy shapes are priorities for Hutton, and if she can't wear pants, she'll choose a dress that doesn't cling or constrict. Reminiscent of the body-conscious knits designed by '70s superstar Halston (who once called Hutton "perhaps the greatest mannequin in history"), this gown ($550) is from OMO Norma Kamali, another longtime legend. Cuff, Patricia von Musulin.
Lauren Hutton in Gryphon New York

West by Southwest
This lived-in look is textbook Lauren Hutton—her clothes always seem like things she's owned and loved forever. The intentionally rumpled trenchcoat (Gryphon New York, $610) works nicely with slightly baggy, tattered "boyfriend" jeans (I Heart Ronson for JCPenney, $44). The mix of rancher casual and Native American craft is, of course, associated with two Laurens: Ralph L. did the plaid shirt (Ralph Lauren Blue Label, $165); the turquoise and silver necklace and bracelet (Vicki Turbeville) look like something Lauren H. might have picked up on her global travels—she collects accessories worldwide and is crazy about "things I bought when I was with good friends that have good stories surrounding them."
Lauren Hutton in Lauren by Ralph Lauren

Suiting Herself
Hutton has a history with menswear, ranging from down-and-dirty denim to Giorgio Armani's slouchy '70s pantsuits, from Calvin Klein's minimalist '80s silhouettes to modern practitioners like Paul Smith (shirt, Paul Smith London, $295), Ralph Lauren (pants, Lauren by Ralph Lauren, $179), and the Olsen twins (blazer, The Row). Balanced proportions—here, the juxtaposition of a perfectly fitted jacket and easy bottoms—are crucial to pulling off anything oversize. Her shoes are Sperry Top-Siders, the boat shoes she made famous: "I like the way they feel. They make you prance rather than shuffle." Ring, Me & Ro.
Lauren Hutton in Ralph Lauren Black Label, The Row and Helmut Lang

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.
Lauren Hutton in Gap

The Natural
"This hat reminds me of my daddy," Hutton says. "He was fighting in World War II when I was born, and I never met him, but it's a real GI hat—I found it in the '60s and have worn it ever since." (It so impressed Revlon's Charles Revson that he had it copied for the Charlie perfume ads.) She also likes the genuine safari shirt from venerable outfitter F.M. Allen ($148): "For years I got my safari clothes in Kenya, from a company where the local police bought their uniforms." Authenticity matters to Hutton, even in makeup: She's supplementing her original cosmetics line with a certified synthetic-free collection, beginning with September's launch of the All Natural Face Disc (11 products in one palette). Sweater, Gap, $70. Pin, available at The Family Jewels.
Lauren Hutton in Theory and Urban Zen

White Lightning
"I want these shoes," says Hutton of the oxford-style lace-ups with a silver patina (Robert Clergerie)—the fusion of menswear and metallic is very much her thing, and great for day or night. Another surprise: the cotton cashmere V-neck sweater swooshing out into a feminine flounce (Theory, $255). Pale, narrow linen-blend pants (Urban Zen, $695) and a tasseled silver bracelet (available at Jacques Carcanagues)—a lot like prayer beads—have a definite Passage to India feeling. Tank, Hanro, $56 .

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