A few weeks ago, I was browsing through an antique store in Philadelphia when I spotted a woman in the accessories section pinning brooches to her lapel. She held up a tiny mirror to see how they looked together against her pristine navy blazer. Eleanor had short silver hair cut into a chic blunt bob and bright red rectangular glasses.
They were vintage; yet timeless. Fashion-forward; yet classic. Everything about her struck that fine balance.
Her ensemble was similarly well-curated: playful yet sophisticated, modern yet timeless. High-low.
Tailored yet surprising. monochrome with unexpected pops of colour.
Everything about Eleanor’s outfit worked.
Not just“Well-dressed-for-her-age” worked. Fashion-person-of-anyage-worked. “I love how those look together,” I said, pointing at the row of triangular pins on her shoulder. “They’re so architectural.” Eleanor smiled and nodded. “Thank you, dear.
I’ve been collecting brooches for fifty years. Bought them new the first time around.” She introduced herself to me and told me she used to be an art professor. As we left the store, she chatted about travels she had taken, art shows she’d seen, and clothes she had bought.
She was 78. But could have been 48. Or 88.
Fashionwise, I couldn’t tell ; or care; what her age was. I’ve been having similar conversations with women ; and now following them on Instagram ; everywhere I go. Just last week I met another stylish silver fox while visiting friends in Chicago.
There’s a whole fleet of them I follow religiously online: Dress the Aging Mother, Authenticallyngo, Age Bang!, MeltingGeneration. Not only are they incredible stylish, they’re shattering the paradigm of what it means to dress “your age.” Instead of letting go of their sense of style once they hit forty (or fifty or sixty), they’re double down. Embracing clothing as a creative outlet, carefully refining their sense of style, and dressing with a freedom that only comes with age and baldly refusing to hide behind mensuration pads and elastic waistbands.
To be clear,I know amazing women in their 20s and 30s who are killing the style game. And I love following Gogo magazine and Lonely Protein for inspiration. But some of the most innovative and exciting outfits I’ve seen lately aren’t coming from teen fashion bloggers, Vogue editors, or Instagram influencers.
They come from women in their 60s, 70s, and beyond; a demographic the fashion industry has traditionally overlooked, mocked,and served exclusively lofty piles of wool beige jumpers and cautious cotton. (“Nice Granny Panties!”) Instead of dressing “Well for their Age,” these women are throwing out the rule book and dressing like exquisite versions of themselves. Empowered by a mixture of life experience, refined tastes, and a learned sense of “who cares what anyone thinks” liberation, women across the globe are dressing with audacity and bravery at an age when society expects them to do the opposite. Sound too good to be true?
Too “Pinterest-ing.? You wouldn’t be the first cynic I’ve tried to convert to the church of Cool Old Ladies Who Dress Well. Go look at the most recent Vogue Runway street style files.
Look past the cluster of 20-something bloggers who were clearly wearing gifted ensembles from NYFW and cheque out the womenCOLORblocking leather trousers with vest dresses. Chunky sunglasses with wide leg slacks. Crochet vestiges atop stiletto boots.
RubberRaindropsOnPondsto Self Portrait jackets with a *hint* of ironic flair. STOP THESE WOMEN ARE rocking outfits that would make half of Instagram drool ; at ages ranging from their late 50s to 80+. This isn’t even just about street-style saints and heirloom-lebritys like Grece Ghamem, Sarah Jane Adams, Jenny Kee and Beatrix Ost (all of whom are absolute heroes in my book).
While we need more accessible examples of fierce matrons with great style, what’s really exciting is that sense of fearlessness seems to be happening on a broader scale. Women Boomers and older are dressing like hell right now and they know it. There’s something magical happening to women who are now in their 60s and 70s.
Many came of age during times of intense style experimentation and change in fashion; the mod 60s, the free-love 70s, the wild-and weird-as-fuck 80s. Many were the first generation in their family to work outside of the home. To delay marriage and children (or not have them at all).
To travel solo. To wear what they wanted with far less judgement and stigma than their mothers and grandmothers had faced just a generation earlier. Add in seven or eight decades of nurturing your personal style; one that you aren’t professional ashamed of (office politics and dress codes be damned!) and suddenly sexism/general misogyny starts to loosen its chokehold.
Many taboos around how women are expected to dress start to fade: what will your coworkers think? What will your husband find attractive? NOW WHAT WILL THESE WOMEN WEAR?! ? “I spent 40 years dressing conservatively for work,” said Judith, a 71-year-old ex-corporate lawyer I met while shopping in Soho who was sporting an Issey Miyake puff-sleeve explosion with trainers. “I can pretty much wear whatever I want now.
It’s incredibly freeing.” Add in enough years doing whatever the fuck you want with little judgement and you’ve got some serious magic feminism dust flowing through your closet. But what are these women actually doing that’s so great? And what can we young grasshoppers learn from their regimen?
After interviewing/style stalking dozens of amazing women over the age of 65 (some famous; some not) I’ve boiled their shared style wisdom down to these SIX KEY LESSONS: SHOP (OR BUILD) YOUR UNIFORM, THEN UPDATE IT WHILE STAYING TRUE TO YOUR STYLE CORE Most well-dressed women over the age of 60 know who they are and what they like. They understand proportions that flatter their shape, colours that complement their skin tone, and pairings that match their personalities. But that doesn’t mean they let themselves get stuck in a style time warp.
One of my favourite parts about meeting women who have obviously invested decades into building a strong style identity is studying how they modernize their signature silhouettes. Whether it’s pairing classic Jackie O sunglasses with unexpected fashions, or wearing clothing that’s vintage yet seems futuristic, they know how to nod to their own style history without looking dated. “It’s basically been the same outfit I’ve been wearing for thirty years,” Maria, a 69-year-old gallery owner wearing massive volume on top with slim trousers and jeans told me. “But I constantly tweak it little by little, whether that’s with silhouette, fabric, or texture.” Maria’s style evolution philosophy is a common refrain: learn your style DNA, thenPeriodically dabbling in trends only when it complements that base and you’ll always stay current without looking like you threw yourself into TikTok’s styling octopus. STYLING IS ABOUT BALANCE: PART SILHOUETTE, PART WORDSMITHING To illustrate this visual balance, I’ll take you through my favourite outfit Eleanor wore during our morning together: black blazer, white blouse, red glasses, navy jeans, black_util/, slouchy trainers, with three geometric brooches layered on top.
Volume/boldShoulder with structured waist and slim legsSilhouettes paired with Structure. Minimalist blouse and jacket with bold glasses and statement broochesStatement mixed with Minimal. Mixing Feminine and Masculine styling.
Basic jeansGrounding basics with high fashion. High-end broochesEclectic Finds mixed with Luxury/High Fashion. Touches of both modern and vintage styles.Modern mixed with Vintage.
Basically, if you remove any one of these factors, Eleanor’s outfit loses it style mojo. Learn to mix the basics with your statement pieces, the contemporary with the vintage, high fashion with found treasures. It’s basic styling grammar.
ELEANOR CONTINUED: BASIC GARMENTS, ACCESSORIZED TO BRILLIANCE Speaking of Eleanor, you might’ve noticed she accented her simple-yet-styled blouse/blazer/jacket jeans ensemble with some pretty badass brooches. These women know how to use accessories to elevate an entire outfit. Because while many of these women have decades-long wardrobes full of amazing clothing, they often choose to build outfits around amazing statement jewellery, cool vintage eyewear, incredible shoes, or unique bags they’ve collected over their lives. “Growing up, my mum wore these awesome bakelite bangles,” said Diane, a 68-year-old artist whose work you should Google ASAP. “She gave them to me when I was thirty, and I’ve been adding to that collection for nearly forty years.
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They just take any outfit to the next level.” Focus on accessories. Stack on that jewellery. Kaftan over jumper.
Blouse under jacket. Dress it up. Dress it down.
Throw on an extraordinary hat. Or brilliant pair of socks. These women understand how powerful a role accessories play in taking outfits to the next level ; and they aren’t afraid to use them.
DRESS FOR YOURSELF, THEN DO SO WITHOUT A SINGLE LIFETIME OF FILTERS This couldn’t be trendbro more important: women over 60 are killing the style game right now because they give AF about what other people think of how they dress. After years* of dressing for men, trying to look attractive to other women, projecting professionalism at work, they’re simply done with it. bored. Over it. “My style evolved from pleasing others to me pleasing myself,” said Carmen, a retired professor whose personal style walks the line between doctor and diva, when I asked her about dressing for herself. “And that feels incredibly freeing.” Clothing feels like self-expression, not penance.
And when you’ve spent decades honing and perfecting your style visage, your outfit game is going to be strong. Consider your Grandma had a closet full of killer clothes she never wore because she was “too old” for them. Now imagine she magically gained the ability to wear whatever she wanted without judgement.
How good would her style game get? *I can’t speak for every woman of course. But I would venture that is true for the majority of women. SHOP WITH THE ENDLESS WARDROBE IN MIND “How did you buy that?” is a common question when talking wardrobe with these femmes.
Clothing isn’t temporary for them; it’s personal. Many of these women didn’t grow up with access to cheaply made fast fashion, nor did they have a habitual opportunity to splurge on trends like we do now. But what they lacked in quantity, they made up for in intentionality. “In the old days you couldn’t buy things as frequently as you can now,” said Patricia, a former dancer in her mid-70’s. “So everything in my closet was something I loved.
I tend to still shop that way.” This mentality shows when studying their outfits: vintage designer jackets thrifted decades ago worn with currently-season trousers or vice versa. Clothes from different eras worn together as if they were from the same time period. Unlike fast fashion-obsessed millennials, many of these women will shop with pieces that can stand the test of time, fit multiple styling formulas, and be worn over and over (and over) again.
BELIEVE IT OR NOT, THESE IDEAS CAN WORK FOR YOUNGER GENERATIONS Yes, this is partly a love letter to awesome ladies who have kept their damn style game strong as they’ve aged. But it’s also an invitation for young readers to learn from their playbook. Age appropriateness is bullsh*t invented by people selling clothes.
If you want to dress like you’re 110 instead of 20, do it. Learn from women who have been refining their style lifetimes instead of trend hopping for years. Invest in classic pieces that will stand the test of time as you modernize them with accessories and occasional trends.
Focus on building a deeply personal wardrobe you love, not just inheriting trends promoted at you by corporations. Balance your statementmaking with easy basics. Focus on accessories.
Buy less. Love what you buy. Dress for yourself.
Sound familiar? Because these are all things we preach here at CherryPicks. They’re just taken to an art form when you have decades of wisdom under your belt.
Trust me, I’m as tired of hearing “Cherries, these’re trends for EVERY generation!” as you are. But we can all learn from these stylish women; whether we’re 16 or 60. Honestly, the trickle-down effect is already happening.
Scroll deep enough on vintage Pinterestboards and you’ll find that “new” trends weren’t invented five minutes ago: they were borrowed from women who owned them before the brands selling it to you revived it as a “must have.” Vintage is the new black. Slow Fashion is gaining momentum. “Unique” is back. One day, millennials will be considered “Old” and they’ll probably dress like their mums.
It’s the circle of fashion. Stylistically speaking, we’ve begun to appreciate what these women have been rocking for decades: well fitted clothes that flatter their shape instead of being sized for the invisible “Model of Average.” Handmade details. Intentional clothing with personality instead of faceless, ephemeral trends.
Clothing as self-expression, not shame. We’re also now seeing more brands using older models than ever before. In a recent ad campaign, Jacquemus featured women of all ages.
There wereかなりイイ感じなold ladies styled alongside models that wouldn’t look out of place on Proenza Schouler’s runway. Valentino, Michael Kors, and Simone Rocha have also all incorporated models over 50 into recent campaigns. There’s even a whole blog devoted to stylish women over 60 (yes, you guessed it, Advanced Style).
Started by photographer Ari Seth Cohen, it’s brought international attention to style icons likeaggio Minturn and now sells t-shirts and home goods featuring iconic images of Eleanor’s beautiful counterparts across the globe. But for every brand shouting it from the mountaintops, there are dozens that still focus exclusively on customer’s under 30.
It’s understandable clothes companies cater to younger consumers.
The majority of fashion buying power is concentrated by people under the age of 34.
But women over 50 still control a huge portion of consumer spending, and their style influence is growing. And despite a recent push for more body positivity and size inclusivity in the fashion industry, age inclusivity is still sadly lagging behind.
Don’t get me wrong, there are fabulous things happening for mature woman in the fashion industry. But we still have a long way to go. And if learning from cool old ladies is apart of that journey, I’m 100% down for it.
Learn from their wisdom. Build your wardrobe around a personal style you’ll love for decades. Mix high-end pieces withFound Clothing.
Focus on accessories. And maybe one day, you’ll join the styleista set of grandmas we all wish we had. Or were….. “I hope you’re not writing about our ‘generation.’ Cause we’re not a generation, sweetie.
We are humans.” – Eleanor, when I told her I was writing this article.
