Growing up in 1940s Charleston, South Carolina, Hutton bumped right up against the code of Southern femininity: "Everything was very proper. It was patent leather and organza." But then her mother became, as she delicately puts it, "downwardly mobile"; they moved to the backwoods of Florida, where Hutton felt free. "I hit the trees. I became a boy-girl. I liked wild things."
Slideshow: See photos of Hutton in cool casual fashion
She landed in Manhattan in the early '60s, a self-described "short, very American, irregular thing" with a gap between her front teeth. (She told her modeling agency she'd fix it, "but I really had no intention of doing so.") The mannequins of the moment were "European swans—giant, beautiful, perfect girls." When Hutton was sent to fabled fashion photographer Richard Avedon, he was dismayed by her inexperience. "He asked me where I came from, what I did. I told him that I ran, played, and jumped in the swamp." So he got her leaping for the camera. Three months later: 14 pages in Vogue.
With her spirited presence and girl-next-door looks, Hutton became a muse for the designers who were then inventing American sportswear—clothes for women who worked and played with as much verve as men. Off-camera, Hutton channeled her energy into daredevil activities like deep-sea diving, dogsledding, alligator wrestling, and motorbiking. No wonder she developed an androgynous style—you can't run and jump in a tight skirt and heels. "It's sexy to see curves under straight-cut men's clothes," Hutton says. "And the stars I liked—Carole Lombard, Marlene Dietrich, Kate Hepburn—always dressed that way."
After a decade of film and TV work, Hutton went back to modeling in her 40s. She realized that most makeup, with its heavy textures and shimmery formulas, was made for younger skin. In 2002 she launched Lauren Hutton Good Stuff, cosmetics that go on invisibly and don't make faces look spackled. (A cheerleader for wrinkles—"our medals of the passage of life"—Hutton is fiercely against facelifts and airbrushing.)
On the subject of age-appropriate fashion, she's less inclined to be prescriptive. She believes in a foundation of classics, but her style advice isn't about shopping so much as figuring out who you are. First, she says, make a candid external assessment: "To put together the best look, you have to use your eyes and brain together." Remember which colors inspire compliments. Identify friends with similar bodies and pay attention to what looks best on them. Pick what pleases you. "And don't buy something because a salesperson tells you to!"
Next: Hutton's 4 ways to develop your personal style