It’s one thing to maintain that attitude when you’re at the height of your powers—or at least grown up enough to be at peace with your looks; carrying it off during your insecure cookie-cutter teen years is another. “I was really gawky as a teenager,” says Libby Edelman, 58, cofounder with her husband of the shoe line Sam & Libby. “I thought curvy was the only thing that appealed to boys and I was never going to be a hot babe. It took me until my thirties to realize what I have, how to accentuate it and enjoy it. That only happened when I stopped trying to dress like everyone else and settled on my own style, which is classic with a twist.” Consider it revenge of the non–prom queen: The lankiness that caused grief back then now gives Edelman a Katharine -Hepburn–like aura of grace and style (evident in the April 2012 issue of More, or at more.com/libby-edelman). “I love how I look so much more now than I did when I was younger,” Edelman says. Marie Josee Lafontaine, a makeup artist with a silvery pompadour and an androgynous aesthetic, concurs. “As a teen, I was just as awkward as other girls, and fashion wasn’t on my radar. It wasn’t until my twenties, when I was working in Paris, that I developed my ‘simple chic’ look. I credit a designer called Irie with helping me understand how practical yet elegant cuts brought out the best in me. And now I still rock that look: tight jeans or pants, loose tops, boots, a jacket, paired with simple jewelry and my vintage man’s Rolex.”
Other women, like Elizabeth Musmanno, the forty--something founder of the Musmanno Group and president of the Fragrance Foundation in New York City, were lucky enough to own the power of their looks early on. “As a teenager, I had my mom sew clothes that made me stand out, whether they were jodhpurs or metallic jumpsuits,” she says. “I had a certain ‘I don’t care’ attitude. I was never going to be the blue-eyed, blonde, buxom girl. But I liked the way I looked. And I liked the guys who were attracted to someone like me.” Vivian Diller, PhD, author of Face It: What Women Really Feel As Their Looks Change, points out that women who relied on more traditionally feminine attributes like lush hair, full breasts and thick lashes for their self-esteem often have a harder time later on because these are all assets that diminish with age. “Good posture, a great smile, the ability to engage someone with your eyes—these are attributes you can maintain for life,” she says.
While confidence and a heady dose of personal style certainly help when it comes to aging, there’s no denying that genetics plays a big role in the Handsome Woman’s midlife victory lap. “The more defined, dominant cheekbone that may be less attractive in youth will stand up better over time,” says New York plastic surgeon Adam Kolker. Dermatologist Patricia Wexler likens it to having better scaffolding, with more architecture for sagging skin to hang on to: “Strong bones, particularly in the cheek and jaw, help maintain the integrity of the face against the effects of gravity." Those with weaker facial structures have less support for the extra, sagging skin that inevitably comes with age, making them more prone to jowls at the jaw or deep folds beside the nose and mouth.
It’s not all the luck of the jaw, though. The Handsome Woman may affect a look of effortless elegance, but beneath it a fair bit of maintenance is going on. “Even if you’ve won the genetic lottery, you still need to practice discipline and balance,” says Judith Sills, PhD, author of Getting Naked Again. “These women have acquired the lifelong habit of taking care of their health, watching what they eat and exercising. They still make the effort. But they balance it by gracefully letting go of the excessive enhancements of youth, whether it’s piling on too many accessories or wearing too much makeup, so that they can let who they are shine through.”