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The Ageless Secrets to Having Iconic Style

Society often frowns upon older women showing off their bodies and taking up space, but that hasn’t stopped these three trendsetters from embracing their personal style—and inspiring others in the process.

By Rachel Simon

Throughout our entire lives, women are told how we should and shouldn’t dress. When we’re young girls, society wants us covered in ruffles and bows, and then as adults, they want us to be an impossible mix of “proper” and flirty (not to mention thin, hairless, blemish-free, and more often than not, white). But when we get past middle age, there’s only one rule for us: Cover up and get out of the way, because no one wants to see older women showing off their bodies and taking up space.

Obviously, these standards are total BS; women (and all people) can, and should, dress however the hell they want to, regardless of gender, age, or race. Yet the fact is, there is a long-held stigma against older women having fun with fashion, especially when that fun entails wearing clothes and accessories that are usually associated with younger age groups.

Post-menopausal women often become invisible in all sorts of ways,” says Hazel Clark, a professor of Design Studies and Fashion Studies at New York’s Parsons School of Design. “They become this sort of blur.” 

But in recent years, societal norms regarding age and gender have slowly begun to lessen, thanks in part to the rise of Fourth-wave feminism and “a greater diversity of options in how we can dress nowadays as older people compared to say, 50 years ago,” Clark notes. Still, for every beloved fashion icon like Iris Apfel (who turned 100 this year!) or TikTok star Lonnie Pike, who have built a massive and loyal following for their unconventional style, there are many, many more women who face criticism for dressing in a way others deem outside of their age bracket. Even for women over 50 who do dress “appropriately” for their age, it’s a lose-lose situation. While they may not be called out for trying to fit in with the youth, they still get reprimanded for daring to remind others of their advanced age and not getting older as “gracefully” (read: blandly) as their male peers. 

Shop similar styles: The Kelsey dress and Leora earring jackets.

The fact that older women—particularly older women above a size 10—make up one of the most underserved markets in fashion makes the challenge of striking a balance when it comes to clothing even more difficult. Gabrielle Carlson, owner of an eponymous boutique in New York, says that she doesn’t purposely dress any of her store’s clients in younger-seeming styles (“I dress a sensibility more than an age,” she explains), but understands the challenges of styling yourself in a way that both looks good and feels good as an older woman. “How you dress is how you impart who you are,” she says. “If [older women] feel there’s nothing there for them anymore,” she continues, “that’s a horrible feeling.”

So if you’re a woman who has “aged out” of fashion on paper, but not in your heart and mind, what are you supposed to do? Well, you might as well throw your arms up in defeat and wear whichever colors, styles, and trends you like, because when it comes to ageism against women, there’s no way to win. Dress however you feel, no matter what others say. After all, fashion is about self-expression—and if that means sporting looks more typically associated with 20- or 30-somethings rather than Baby Boomers? More power to you.

Below, we spoke to three women over 50 about their personal style, the confidence it gives them, and what they say when people say, “you’re too old for that.”

Lyn Slater, 68

Founder of Accidental Icon, a fashion site geared towards urban women with an Instagram account boasting over 750,000 followers.

“I am famous for rejecting categories and boxes fashion tries to put me in.” 

What “youthful” clothing means to her:I have always dressed to express the person I am inside, experiment with identity, and convey how I feel about the time I am living in. That’s my style, and I wouldn’t characterize it as youthful but rather authentic.”

What she wears:Jeans, sneakers, and oversized shirts are my go-tos.”

Why she dresses “young”: “There is often a disconnect between the age older people experience themselves inside—more vibrant and youthful—and their chronological age. There are days I feel 25, others 40, and some 68… I see all clothing as neutral when it comes to age.” 

What she loves about her style: “I get dressed to suit my mood, how I feel inside, and the goals I want to achieve on a particular day. When I dress that way, I feel confident and centered.”

What she says to haters: “You shouldn’t be afraid to get old, as it’s a time for wonderful adventures. And clearly, due to the large following I have, there are many who admire how I dress.”

Shop similar styles: The Theo sweater, Mejia pants, and Koio sneakers.

Judy Fertel, 56

Owner of Bridge House Vintage, an antique shop in East Chatham, NY.

“I definitely dress youthfully, and I wouldn’t have it any other way.”

What “youthful” clothing means to her: It’s clothing that is spirited, unique, personality-driven, and non-conforming.” 

What she wears:I still wear high-top sneakers… I wear vintage jewelry mostly from the ’60s and lots of ’80s baggy pants with concert T-shirts that I’ve had forever. They bring back such good memories of my youth. Why throw these things away?” 

Why she dresses “young”: “My parents always encouraged me to be unique and never had an issue with my style of dress, so it stayed as my mindset into adulthood. This way of dressing has always been my style, and I have not adjusted it as I aged.”

What she loves about her style:I feel good about myself knowing that I can still wear whatever makes me feel happy and am often complimented for my look.”

What she says to haters:People need to think less about what others think and just be themselves.”

Arlinda McIntosh, 63

Founder and Creative Director of the New Jersey-based Sofistafunk—TheSkirt Co.

“Who am I hurting? I’m doing something that I like doing.” 

What “youthful” clothing means to her: “I see fashion as just clothing. It’s not about age. That’s just something that we’ve been taught. If I have it on, then it’s for me.”

What she wears:I wear a lot of big skirts, because I love volume. I have a denim skirt that I wear a lot that has a train on the back, and my hair right now is blue and pink and green and a little bit of yellow.”

Why she dresses “young”: “I never, even as a child, listened to anyone other than my mom tell me what I can’t wear. You only have so many years, and we don’t know how many there are, so enjoy what you have while you have it.” 

What she loves about her style: “It’s not for people, it’s for myself. You can’t live for people, because if you live for people, you die unhappy. Look in the mirror, and if you like what you see, then you should just go. That’s what I do.”

What she says to haters: “Don’t let it matter what race, what gender, what color, what anything. Just be, and let people be. And if it bothers you that much, ask yourself, ‘why does it bother me that that old lady is wearing a dress that looks ‘young?’”

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