Last month, I was browsing through a vintage store in Philadelphia when I spotted someone doing something most women (myself included) often stop doing after a certain age: playing dress up in the retail store. I was lingering near the accessories when a woman caught my attention. She was trying on jackets, holding various brooches up to the lapel of her perfectly tailored navy coat, examining herself in the small mirror.
Her hair was short and silver, cut in a razor sharp bob. Her glasses were wide red frames, vintage-y but not old-fashioned. She wore bright colors and interesting textures, but in such perfect proportions that the overall effect was somehow classic.
Not just “good-for-her-age” classic—everything about her attire refused to be pigeonholed by number. Fashion-person classic.
“I love how those look together,” I said, gesturing to a cluster of oversized geometric brooches.
“That composition is perfect.” She looked up at me and smiled. “Thank you, dear. I’ve been collecting those for fifty years.
Bought them when they were new the first time around.” She was Eleanor, a retired art professor who managed to look far cooler than I will probably ever in her lofty, old lady height of 78. She spent the next hour schooling me on how to dress with legitimacy and flair past the arbitrary age society assigns for that milestone. Over coffee.
She told me more insightful observations about modern fashion in those sixty minutes than I had read in many recent trend forecasts. And she wasn’t keeping up with trends. She was four decades ahead of them, effing whatever anyone else thought about her outfits.
Eleanor is hardly the first stylish septuagenarian, octogenarian, or nonagenarian I’ve met to blow my mind. Quite the contrary. Something I’ve noticed over the past few years is that some of the most exciting, innovative dressing happening right now isn’t coming from Kylie Jenner copycats or influencers half our age.
It’s coming from women in their 60s, their 70s, and beyond—a group largely written off by an industry that dresses them like grandparents or sexually stereotypes them into micropages on retailers’ websites. When I think about the coolest, most creative women I know who are older than me, I’m struck by how they don’t dress “well for their age.” They just dress REALLY FUCKING WELL, period. They wear things I want to wear; they push boundaries I never knew 60+ women could push; they experiment with fashion in ways I think we tend to stop doing as we get older, safe in the comfort of our (“safe” is used very loosely, here) uniforms.
And they’re doing it with an authority, creativity, and freedom that can only come from having spent decades refining your personal style combined with a learned indifference to what the fuck anyone else thinks of you or what you’re wearing. If you don’t believe me, consider: Photographs of the most stylish street style sightings from recent fashion weeks are increasingly graced not by twenty-nothing instagrammers rocking full-NYC price-tag wardrobe submissions, but by women like Grece Ghanem (mid-late 50s), Sarah Jane Adams (60s), Jenny Kee (70s), Beatrix Ost (80s), Amanda Levitt (70s), or Lisa Fox (50s). They aren’t afraid to wear something wild, exciting, colorful, impractical, expensive, or avant garde.
They aren’t trying to look young. They are just, quite literally, the best dressed women in the room. Period.
This, I think, is reflective of a larger trend happening with this current generation of women in their 60s, 70s, 80s, and beyond. Sure, there are some wildcards in every generation, but this group of women, in particular, is killing it in the style department. Why?
Well, for starters, they grew up during some of fashion’s most creative, innovative periods: the mod tilt-and-whirl dresses and pillbox hats of the early 60s; the bohoexperimentation of the late 60s and 70s; the flashy power dressing and messy-androgyny of the 80s. Hell, some of these women even had successful careers when wearing pants was considered a radical statement for women. They were some of the first women in their families to graduate college, travel abroad alone, work full-time careers, wait until their 30s to get married or even choose not to have children.
They were young adults during some of fashion’s most exciting periods of innovation—and they continue that innovation into their own personal style today. In addition to growing up during some of fashion’s most exciting eras, they’ve also had decades to refine their personal style. And now many of them have reached an age where they literally don’t give a fuck what society thinks of how women should dress.
Some of the restrictions women encounter wearing whatever they want (office dress codes, parenting pressures, marrying people older than them telling them what they should and shouldn’t wear, the male gaze, etc.) start to fall away as you age. Suddenly you care less about what people think of your clothes and more about wearing exactly what the fuck you want. The results, quite naturally, are incredible.
“I spent 40 years dressing for a male-dominated corporate office,” said Judith, a wise-beyond-words 71-year-old former corporate attorney I recently met. “I wore high heels and button down shirts and suit pants day in and day out. Now I get to wear whatever I want, however I want to wear it.
I’m exploring clothing with more creative freedom than I’ve ever known.” The combination of caring less about what everyone else thinks + decades spent curating incredible personal style = magic. OK but what *does* that magic style look like, and what can we all learn from it? I surveyed dozens of amazingly stylish women over the age of 50 (please know that I started at 50, not 60 or 65—you’ll see why in a minute) for the answer.
Some are household names; many are not. All are extremely cool. And here’s what I found they tend to do differently than the rest of us: Remember how I said we should start at age 50?
Well, that’s because my main takeaway from researching this article is that you really should start working on developing a personal uniform EARLY. I didn’t realize how crucial having a tried-and-true personal uniform is to aging stylishly until I started talking to women who’ve spent decades refining theirs. Think of it as putting savings into a retirement account, but for your outfit.
Sure, some people’s styles change radically as they age; I’m talking about the women who maintain a particular look throughout their lives, while keeping it feeling current rather than dated. “They’ll know their asymmetrical cut makes their waist look small, that pink jacketとう gener ihommensche trousers create the exact silhouette they like, or that orange looks especially vibrant against their skin,” said one designer I spoke with, who has studied older women’s dressing habits for years. “Once you know what works for you, you can play with that.” “They have decades of refining what works and what doesn’t,” added one stylish friend of mine.
“But the cool ones know how to shake it up inside that framework without totally starting from scratch each season.” Emma Hill, former womenswear designer at Calvin Klein and presently the Womenswear Design Director at Max Mara, agrees. Hill told me that what’s interesting about some of these women is how they tend to have very distinct “uniforms” they repeat over and over—but that those uniforms evolve slightly with time. “It’s the same silhouette they’ve been wearing for twenty, thirty, maybe forty years,” Hill said.
“But maybe it’s with different details, proportions, fabrics, under layers, makeup, hairstyles. Everything around that core look changes, but they know their neutral color palette with leather jacket, chic boyfriend jeans, and white blouse works for them. So they don’t fix what isn’t broken, but they also aren’t afraid to modernize those looks by adding new details that keep their established personal style feeling fresh.
“. On top of knowing exactly who they are and what works for their body, amazing 50+ women also have what I’ll call “stylistic equilibrium.” Translation: they know how to balance many different aspects of a look in one outfit. Bold with subdued.
Volume with tailoring. Statement with basics. Feminine with tomboy.
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Vintage with modern. High with low. etc. It’s what makes their outfits so interesting to look at—they have many different parts pulling in different directions, but somehow everything balances perfectly.
Curled up jacket with prim pencil skirt? Neutral coat with bold bottoms? Tight bodice with wide legs?
Contrast always makes things more visually interesting, and these women have mastered it. “I think of getting dressed as building a sentence,” Eleanor told me over coffee. “You need consonants and vowels.
All consonants is jarring, all vowels sounds singsong. Balance.” Eleanor’s comment about sentence-building rings true when thinking about how women who dress well for decades tend to balance two other competing style forces: doing things how they’ve always done them vs. trying new, rebellious things. With age comes the confidence to choose which parts of what society deems “beautiful” they actually care about, and which they don’t.
They do fewer things just because everyone else is, and so their style tends to remain as they like it, not what society dictates females should like. “I wore skirts for 35 years because that’s what women wore,” said one stylish veteran I spoke with. “Until one day I decided I didn’t have to.” Add it all up and what you get are women who edit their wardrobe down to things they truly love wearing, then rotate those favorites and experiment with them year after year: “I used to buy cheap fast fashion when it was all the rage,” said Diane, a 68-year-old artist I met at the Vintage Vogue exhibit at the Brooklyn Museum.
“Now I know better! I spend more on certain pieces that I know will last, and I reuse them in a hundred different ways.” One obvious perk of taking decades to curate your wardrobe? The stylists I spoke with all know how to spot truly high quality pieces when they see them.
Plus, when you buy less clothing overall, you naturally spend more time researching what you will buy. You begin to truly understand clothing. It’s no coincidence that many of these women can spot a designer garment buried in the racks at a vintage shop.
Building a truly impressive wardrobe doesn’t happen overnight. Or even over a decade. It takes years of curating, collecting, editing, and playing around with clothes.
Think of these women’s wardrobes as museums and theirselves as curators. They’ve spent years stockpiling clothes they love (and will continue to wear years from now), so they have endless possibilities when getting dressed each day. This focus on building a wardrobe over a lifetime—you rather than fast fashion—extends to accessories, which many of the stylish women I spoke with told me they focus far more on than the actual clothes themselves.
Many have been collecting jewelry for decades, from timeless Chanel pearls to vintage souvenirs from overseas. Many have expensive eyeglasses they’ve been wearing since before glasses were trendy. Many wear hats or make funky footwear central to their outfits instead of an afterthought.
“I’ve been building out my collection of vintage bakelite bangles since my mother gave them to me when I was 30,” said Diane. “You should have seen her face when I said I didn’t want her vintage jewelry, I wanted her bangles.” Where do you start to build a wardrobe that will last for decades? Start with a capsule closet, then build out from there.
Here’s what I mean. Buying one great shirt that you know will last for years is far more impactful than buying five shirts that will be worn once then thrown out. Unfortunately, society has conditioned us to think of clothing as disposable (seasonal trends, people! ), when in reality buying better and buying less will help your wardrobe hang lasting longer than you can imagine.
“I love mixing high end things with vintage I found in Thrift Town when I was in college,” said Tamara Mellon, founder of the luxury shoe line hunny. “Clothes should be fun, not stressful. If you find something that you love and that fits well, you should buy it.” Buying less, choosing well, and sticking to a clear idea of what works for you (your personal style!) are all important factors in dressing well as you age.
But what’s maybe most important is something money can’t buy: a willingness to let go of what other people think of you and your outfit. “My friends are always commenting on how I dress like myself and not for anyone else,” said one stylish source I spoke with. “I spent too much time doing otherwise when I was younger.” “The older I get, the less I care,” added another stylish woman.
“I’ve let go of pleasing everyone.” It’s no secret that many women feel like they can no longer wear things as they age. “Dressing for yourself” is something we’re told is vain, egotistical, or somehow defiant as women get older. We should be wearing knee-length skirts, or pant suits, or faded tees and jeans.
But what if we decide that as long as we feel good wearing something, we don’t give a shit what anyone else thinks we should wear? This idea of dressing purely for yourself is something that seems to be ingrained in many stylish women as they age. Not only are they dressing without outside influence, but many are dressing without regard for age norms at all.
They’re not dressing like youthful trends tell them they should. They’re not dressing like their 30-year-old selves would have. Hell, they’re not dressing like everyone else their age is.
One of my favorite street style shots from recent seasons belonged to…wait for it…81-year-old Lauren Hutton. Wearing an oversized black blazer, gold jewelry, sheer black top, and black cigarette pants. She could have been on the streets of Paris or Brooklyn.
She just looked like Lauren mother f****** Hutton.
And that, friends, is the secret sauce of ageless style. When I asked fashion historian Ilaria Venturini Fendi for her thoughts on what women are doing right as they age, she said it all boiled down to confidence.
“If you want to dress agelessly, you have to get to a place in your life where you feel ageless,” added my buddy Lisa Fox. “Like you can wear whatever the hell you want and own it.” What I loved most about interviewing women over 50 for this article was realizing that they’re not trying to look young. They’re just dressing exactly how they like, thanks to decades of figuring out what brings them joy in clothes.
So the next time you’re searching for outfit inspo online, look for it in the recesses of your own closet. Dust off that vintage Chanel jacket your grandmother gave you or make that floral print midi you once hated your new favorite. Buy less.
Buy better. Build a timeless capsule wardrobe. And dress yourself.
No one is going to dress you like you can at your age.
