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How to Dress Over 50. Hint: Don’t Make It a Thing

Style over 50 can be confusing if we listen to all the conflicting advice. But maybe we already have the answer.

A friend/creative partner/soul sister and I chat on the phone each morning. Over coffee, we discuss everything from politics to funny memes to Ozempic face and back again. It is often hilarious; this is my way of manifesting a podcast for us. We have already given it a name. And that is, “Everything is a thing,” because isn’t it?

Have you all noticed that we have become obsessed with making a big deal about everything? Perhaps it has to do with our 24/7 bloodthirst for news and content, or it’s more about the hyper-hysteria that makes me feel like every newscaster, news outlet, and TikToker is a crazed Jewish mother (trust me, I have one). Still, my friend and I are sick of everything being a gosh darn thing.

Take aging as a broad construct; precisely, how to dress over 40/50/60 and beyond.

One piece in Fast Company touts Frances Valentine, a label founded by Kate Spade and her partner that focuses on a sort of Lilly Pulitzer construct of how older women should dress. BRIGHT. BOLD. MARTINI WORTHY. I’ve been to their shop on Madison Avenue, and it’s dopamine inspired. But alas, a bit too Palm Beach for my more metropolitan taste.

Then the Guardian published a recent piece that noted that style for women of a certain age could feel very confusing. On one hand, we get pissed that designers are not speaking to us. On the other, don’t speak to us as if we’re old. Add in social media overload and the relentless pursuit of the “must have,” and we have a meltdown. It’s a wonder any of us know what to wear.

Photo by David Stewart

But one thing most fashion pundits agree on is that you should buy better and less, stick to brands that suit you, and that, as millennials hit their 40s they’re going to take fav brands like Everlane and Cuyana along with them. I think that’s a great strategy, particularly for brands like the two I mentioned who have an ageless appeal.

To add to all this confusion, I happened to catch Justine Bateman on the Today Show this morning, talking about how she won’t alter her face to please society and its notion of what aging should look like. Sitting in her kimono, fishnets, huge hoop earrings, and overdone eye makeup, I thought she looked beautiful but odd. And that’s because my overstimulated eyes are not used to seeing a woman age naturally at this point, particularly on live TV — shame on me. It’s like I didn’t recognize a face free of derm visits, which is ridiculous.

My point? Can we stop making how women age and what we wear a thing?

My take is simple.

I have a well-honed sense of style I’ve been crafting since early childhood

I realize I have a well-honed sense of style I’ve been crafting since early childhood. Style has always been part of my identity, and it continues to be a fun way to express myself and share my point of view with the world. I mix high, low, and everything in between. I pay attention to trends because they inspire me, but I look at them less dogmatically and more pragmatically. For instance, I’m not wearing a dress with a cutout. Full stop. But will I go for a crocheted mini dress in the summer? You bet.

I also have the advantage of never having had to truly “dress” for work. As a lifelong creative professional, I have always been lucky to wear what I want. And that’s something I thought of last night. Many women get confused over what to wear at midlife and post-midlife because they have different markers than mine. I have never had children, and I have never had a conservative corporate job. And I have never thought about how my look needs to change as more and more rites of passage come my way. 

Photo by David Stewart

For those of you who may be retiring or empty nesting, identity may play a role in a style crisis, but let’s stop making it all a thing.

Justine can laugh off her lines with pride, and anyone else can get poked with botulism on their eleven lines if they please.

I suppose it’s true I wouldn’t have a column if mature style weren’t a “thing,” but can we maybe just take a deep breath and have some fun? Perhaps if we lighten up a bit and stop staring at ourselves and social media with such a gimlet eye we can just realize that nobody needs to tell us what to wear or how to wear it. What I love about this column is that I get to share all the things I love without being too preachy or prissy.

Once you reach a certain age, you’ve tried it all and you know what your vibe needs to be

I met my friend who is over 70 for dinner last night, and she looked terrific in a down vest, fatigue pants, a patterned silk scarf gathered at the neck, and a simple sweater with the most lovely red lip. That’s essentially timeless, and that’s the thing. Once you reach a certain age, you’ve tried it all and you know what your vibe needs to be. Esprit, a brand I was more than enamored with as a pre-teen, has relaunched and now has a pop-up in Soho. And while it gave me great joy to see one of my favorite brands relaunch, there was not one thing in there I would wear for myself, though I saw many things that made me momentarily wish for a daughter so that we could discover this iconic brand together. 

I suspect that if fashion/style is throwing you, you may be rethinking lots of other, admittedly more important, stuff in your life, like where to go next in your career, relationship, and home. For me, this is the most “me” I have ever felt, and a little botox or a more expensive pair of trousers can’t shift that. So here is my mantra for you to repeat as you stand having a hot flash in the Nordstrom dressing room:

I will wear what I please, and I know who I am.”

Style, like everything else, has gotten too serious. Chances are you’ve tackled a lot of important stuff in your life. From heartbreak to heart songs, you’ve got this, and you don’t need a brand or celebrity or me to tell you otherwise. Aging is a thing, and no hysterics are necessary. So whether you’re Team Frances Valentine or Team dancing around your living room to Frankie Goes to Hollywood, RELAX. Getting dressed doesn’t have to be confusing when you trust your gorgeous self to wear and be entirely you and trust you are right where you need to be. XO

See medical disclaimer below. ↓


  1. I love every word of this and find myself skirting the fine-line between clutching the skinnies and middle-part-or-nothing. But I hard-rolled my eyes when the internet exploded- then anointed- Justine Bateman as the “natural face” poster child. What is more rare to me than seeing a natural (and very attractive by the way) face aging is to see it surrounded by so many ill-suited style choices. Unlike your fabulous 70-year-old scarf wielder, Justine is selecting make-up and styles that don’t suit her. The heavy black makeup would make a 15-year-old look tired and washed out, the choice of fabric and colors detracts from her beautiful olive skin. Yes her hair is gloriously dye-free but she was genetically blessed with full, dark hair which many women aren’t. This isn’t a natural aging moment to me so much as a no-natural-sense-of-style moment. Live your vibe… but why not suit your coloring along the way? P.S. Let me know when Everything is a Thing drops so I can pretend I’m on that enviable party line

  2. I love this! So many midlife women are struggling to dress to remain visible when what they need to do is listen to their gut and embrace who they are. Too many conflicting messages are confusing and women begin to question their judgement. If you feel confident wearing it, that’s what matters.

  3. Like you, Sheri – been in a creative field all my life, so vintage /high/low/ dressing is still my de rigueur approach.

    When I hit my 50s I started really looking at older women – out and about /on the street /at the store etc —-knowing that was my future.

    I particularly grew to admire (and made a point to tell them so!) the older women who put in that “extra effort”to look great. And I noticed it had nothing to do with the particular style or even economic status – just caring about presenting themselves with panache . As a result , they radiated their particular brand of beauty!

    However, unfortunately, I also observed the opposite; other mature women who seemed to “let themselves go”, falling into apathy about aging and giving up on themselves and their once attractive appearance..

    Now in my 70s I am committed to be one of the “put a little effort in” older women.(and god knows it does take EXTRA effort as we age, I confess!) I still see fashion as fun and self expression . And find that my effort now is appreciated by others; for younger men and women —-strangers—-often compliment me on how I’ve put myself together that day.

    And as much as I appreciate it … what’s really nice is I see them uplifted and smiling as they tell me .

    Because, whether we like it or not, the truth is when we step outside our homes —— we BECOME the environment.

    So the question becomes; “Do we uplift the environment and those in it by putting in “a little effort “ into how we dress ? Or do we bring that environment down?

    We may not see ourselves, but others have to look at us ?! So are we saying “ let me brighten your day?” or are we saying “ f-you , who cares?”

    When we think of the effects (positively or negatively ) we can make on others by choosing how we present ourselves … then really “ everything becomes less of a thing”! too,

    Loved your article – got me thinking …

  4. So loved reading this as it really resonates with me. As do the comments, especially that of Ms Christopher Callen. I too fall into this category of the aging person. I have always felt that if you are going to get dressed anyway, make it a good effort. Feel good about yourself and even give yourself some joy in the process. And yes, others may find some joy in that too. Better to feel good and help put a smile on someone’s face than giving up yourself and fading into that invisible field that often comes with aging. Be the the beautiful flower in the field.

  5. I’m “with you”. As a woman well over the age of 50, I do and have always dressed as I please, and I love everything about the statement : “Don’t make it a Thing”. A relatable article, thank you.

  6. Lovely article. The peace in aging is we grow confident in our choices after seeing trends come and go and knowing what suits us and where we enjoy, but take a pass, on clothing and makeup styles of the moment. What do I notice most among my aging friends and young friends? The spark in their presentation to the world – kind eyes, genuine smile, sincerity and enthusiasm for life- best fashion statement ever!


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The ideas expressed here are solely the opinions of the author and are not researched or verified by AGEIST LLC, or anyone associated with AGEIST LLC. This material should not be construed as medical advice or recommendation, it is for informational use only. We encourage all readers to discuss with your qualified practitioners the relevance of the application of any of these ideas to your life. The recommendations contained herein are not intended to diagnose, treat, cure or prevent any disease. You should always consult your physician or other qualified health provider before starting any new treatment or stopping any treatment that has been prescribed for you by your physician or other qualified health provider. Please call your doctor or 911 immediately if you think you may have a medical or psychiatric emergency.

Sheri Radel Rosenberghttps://unapologeticstyle.substack.com/
Sheri Radel Rosenberg is a Philly-born, Brooklyn-based writer who explores style, beauty, culture, and midlife with wit, warmth, and wisdom. Her story includes successful forays in the worlds of trend forecasting, ad agency photo production, ghostwriting, and strategic messaging development for fashion and beauty brands - all while amassing a slip dress collection that would make any Gen Xer proud. At the dawn of social media, Sheri launched her personal blog–which combines her passion for writing with her style obsession–and she hasn’t looked back. As Style Editor for the AGEIST, she’s inspired by the styles of the 70s and the 90s, along with all the beautiful people she sees daily in NYC.


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