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
Feeling good, for her, is the touchstone of style, and she cultivates it. Long an environmental activist, Hutton has found her own piece of earth: After a near-fatal motorcycle crash nine years ago, "I needed a softer place to live than New York City concrete, so I bought a 1917 beach shack in Venice, California. It has a big vegetable garden. It's great therapy. A garden responds. You see things change and grow."
Evolution is something of a Hutton trademark. Even with a knee brace from a surfing injury and a business that keeps her more tied down than she'd like, she continues leaping into the unknown. "The doctors told me I'd be fine if I play only golf and tennis doubles for the rest of my life," she says with a laugh. "But I dive. I dogsled. I trek. I guess I'll have surgery." After all, you don't get to be an icon by standing still.
Express Yourself: A few words of wisdom from the master of personal style.
* On wardrobe essentials: "Always have a navy blazer. White pants, tan pants, navy or black pants—whatever looks good on you. Well-made T-shirts in long and short sleeves. And a good pair of black heels and camel-colored oxfords. If you can afford to, get high-quality classics so you can wear them forever and ever."
* On basic black: "It wipes me out. I can't wear it. Not everything works for everybody."
* On biker chic: "Motorcycle clothes need to be thicker. When you're going fast on the highway, you don't want to leave skin behind."
* On accessorizing: "I have small bones, so I can't wear big jewelry. The jewelry ends up walking around. I want Lauren walking around."
* On developing a signature look: "When I first came to New York, my favorite outfit was a pair of aqua terry cloth shorts and a men's maroon mohair sweater. All I'm saying is that you couldn't have been dumber than me. Finding your look isn't complicated if you go in without being frightened. Notice what people are complimenting you on. Experiment with new things once in a while, but have your tried-and-true pieces that work."