In the Shondaland series Living on the Edge, we’re taking a look at trailblazers taking risks in every area from fashion and science to photography and botany to writing and extreme sports. Revealing the most intimate details of your life and challenging norms can be terrifying, but these pioneering spirits are leading the way.

Age, as the saying goes, ain’t nothing but a number. Yet that number can definitely start to feel like more than nothing as we age; for some people, the number can feel limiting — particularly in a culture that prizes youth.

While we can’t do anything about the number, the way we view our age is entirely within our own control. Aches, pains, and the hard knocks life can hand us aside, we’re able to feel just as spunky and fierce at 55 as we were at 25. One way to capture and express that feeling is through clothing. Defiant, artsy, tough, playful, our lewks tell a story, and stories, after all, are timeless. Indeed, some of us dress better as we get older, thanks to hard-earned knowledge of self and the means to afford the things we want. As these three women show, you can be fearless with fashion forever.

Kim Wadsworth, 69

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Kim Wadsworth is pictured at headshot.


“Ageism is annoying,” says Kim Wadsworth, who’s been a makeup artist and stylist for more than 30 years. She turns 70 in July, an age the New York City native and former model once bristled at but now shouts proudly from the rooftops. “I’m trying to change the face and response to a certain number. Who cares? I don’t subscribe to a number. It’s about the energy and positive attitude and embracing what I call your ‘higher half.’”

She wears it well. Her fearless approach to fashion looks both timeless and contemporary — with a willingness to take on clashing patterns, bold prints in trendy silhouettes, and a skin-showing bathing suit. She now lives in Virginia Beach, where she works as a personal shopper for clients, in addition to styling, makeup, bridal consulting, and much more. “I am crushing it seven days a week,” she says. “The paradigm has changed. I’m really trying to show women that just because you’re turning 50 or 60 or 70, that doesn’t mean you get to be lazy and not give a damn.”

She believes style is important and integral to life at any and every age; case in point, her longtime friendship with Iris Apfel, the 101-year-old fashion model and influencer celebrated for her outrageous fashion sense, whom Wadsworth has accompanied to shows at New York Fashion Week and trips to France.

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Kim Wadsworth is shown with her friend, Iris Ipfel.

Kim Wadsworth

Like her friend, Wadsworth employs a few style tricks to ensure that whenever she enters a room, eyes land on her. For starters, a good pair of statement frames. “I change up my lenses with my outfits,” she says, adding that glasses are a good way to punch up an otherwise sedate outfit. Also, statement jewelry. As her Instagram shows, Wadsworth lives for a chunky necklace and a scene-stealing ring; her favorite is an oval turquoise piece that’s become her new signature.

Another tip: “Change your hairdo! I know women who’ve had the same hairdo for 30 years! You can do a side part, bangs. … Try to step out of your box. Embrace color or looks you never considered trying,” she says. Oh, and another thing: “Don’t ask some 20-year-old for advice. I see this all the time, older women seeking advice from their younger daughter, who’ll say, ‘Ooh, Mom, try this!’ And it’s too low. You don’t want to look like you’re trying not to look your age.”

This stage of life, she says, should be about enjoyment — especially enjoying yourself. “Wherever you are in life, stop and look in the mirror. Embrace who are; be grateful you’re here and healthy. What you wear is a reflection of how you feel about yourself.” She says that often when she’s consulting with women or styling, she finds that women can be their own worst critics. “Someone said to me recently, ‘I’ve gained 40 pounds. I know you won’t find anything for me.’ When I hear that, it stops me in my tracks. When I do makeovers, I ask people all the time, ‘What are your favorite things about yourself? Legs? Posture? Whatever it is, we start there.’ Confidence and exuding love of self is everything.”

Nancy Pendleton, 66

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Nancy Pendleton is pictured in one of her many stylish looks.

Nancy Pendleton

When Nancy Pendleton, an artist based in Phoenix, says she doesn’t play by any rules when it comes to her wardrobe choices, she really means it. She’s got a sizable collection of fabulous coats — a not particularly useful stash in one of the warmest cities in the country.

“My wardrobe isn’t necessarily practical,” she tells Shondaland. “I like fancy things.”

Pendleton’s love for clothes and the art of getting dressed is perhaps not surprising, given her background. Beginning her career as an illustrator and graphic designer, Pendleton spent 13 years as an illustrator for The Arizona Republic newsroom before quitting to paint full-time, and her love of bold colors, patterns, shapes, and textures comes through in the larger-than-life ensembles she wears, often to everyday places. “Aside from being hot in Phoenix, we are an extremely casual place. A lot of days, I’m in the studio. And [there] it’s a variation of jeans and a T-shirt because I’m painting. But I’m not afraid to overdress for situations. I’m wearing what makes me feel good. I want to express myself.”

At 66, Pendleton has long since abandoned the limitations and confines she might’ve had in her younger years. Particularly in the decades she worked an office job, Pendleton obeyed edicts both implied and explicitly articulated for women in the workplace, but those days are long over. Her mid-60s have afforded her the ability to buy what she really likes without having to fret over cost or limit her search for designer threads to the sale rack. “If I love something, I’ll buy it and leave it in my closet till I can wear it,” she says, “and I consider it part of my collection.”

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Nancy Pendleton is shown in a fashionable ensemble.

Nancy Pendleton

Among her favorites: pieces by Alexander McQueen, including a top she proudly showcases on her Instagram as the same one Beyoncé wore on the cover of British Vogue. Among her other greatest hits showcased: a showstopping all eyes on me” coat; a voluminous, airy, blood-red skirt McQueen skirt paired with a leather bolero that’s very Carrie Bradshaw; and a deconstructed black-and-white cape over a silk Gucci blouse that creates a playful, off-kilter vibe. Though a good deal of her collection is from high-end designers, Pendleton also loves scouring vintage shops; good finds are less about the label and more about the statement the clothes make and how they make her feel.

For a lot of people, their 60s tend to be a time when they become more conservative with their appearance and choose to take less sartorial risks. “At 66, a lot of people think you should give up on fashion or looking good or having fun with it,” she says. “But why wouldn’t style get better with age? I know what I like. I’ve lived longer and seen more things — I know my shape. I have money now. I have lived my life, and I’m still working. I just have a lot more freedom.”

Lauren Messiah, 42

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Lauren Messiah is pictured during a fashion photoshoot.

Arielle Levy

Stylist and entrepreneur Lauren Messiah has been helping people get dressed and upgrade their closets for 17 years; some 6,000 women and men of varying ages have consulted her on how to look their best, and through her experience, Messiah says there’s no question about who gets the best-dressed trophy.

“Women in their 40s, 50s, 60s, and up are the most fabulous,” she says. People in their 20s and 30s tend to ask a lot of questions (“Should I wear this? Can I wear this?”), whereas women in their 50s and 60s just post their outfits. “They have no f–ks to give. They’re taking more risks.”

That includes her too. Mosey over to her Instagram — where she promotes her business Style Boss Academy and offers tips to fellow stylists and everyday dressers alike — and see how her “no effs” vibe translates to inspired, funky looks unbounded by rules. Take, for example, this fierce combination of a black leather motorcycle jacket with a dramatic denim mini — in the company of Christian Louboutin himself, no less — or this over-the-top combination of baggy sequin trousers, a deconstructed T-shirt, and statement Crocs.


Lauren Messiah is shown with a rack of her styles and outfits.

Arielle Levy

“My style is unhinged,” she says, a mood that she adopted after the lessons (and mistakes) of her 20s and 30s. “When I was younger, I was worrying so much if I didn’t have certain brands, like in high school where you’re trying to keep up. Or hyper-fixate on ‘I’m supposed to meet the one! What if he finds me in oversized wide-legged jeans?!’ Now I’m like, ‘Who cares?’ Life is too short. If it looks good, I’ll wear it.”

Many of the old rules no longer apply, but there are some guiding philosophies the businesswoman and author of Style Therapy abides by. First and foremost, she says, dress in ways best suited for your lifestyle. As a woman with no kids living in the liberal, anything-goes metropolis of Los Angeles, she has choices that would not be the same as, say, for a teacher and mother of three in Wisconsin.

“Maybe the micro mini isn’t appropriate,” she says. “Rules don’t apply to every situation. When you’re older, you know yourself, your goals; you have that discernment. People who are thrusting their idea of what a certain age looks like — that’s based on their experience, not yours.”

Malcolm Venable is a Senior Staff Writer at Shondaland. Follow him on Twitter @malcolmvenable.

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