Effortless Style After 60: The Art of Not Trying
“The art of not trying.” It’s a phrase having a real moment right now, and it struck home with me the second I heard it, Why? Because it’s the thing I’ve been working toward in my own home and closet for years without ever having the words for it.. There’s a moment in every room, and every outfit, where you can feel someone trying a little too hard. The pillows are too matched. The jacket is too pressed. Everything is coordinating so hard it forgets to be alive. I’ve spent years, in this house and in my closet, working toward the opposite of that, and it took me a long time to understand that effortless style after 60 isn’t about trying less. It’s a different, quieter kind of effort altogether.
Ralph Lauren, who has built an entire empire on this idea, put it better than I ever could: he’s said that it’s ‘easier to follow fashion than it is to have personal style’. That’s the whole thing, isn’t it? Fashion is a set of instructions. Style is a set of decisions, yours, made slowly, over years, until they stop looking like decisions at all and start looking like you.
The effort that isn’t supposed to show
Here’s what I think can be misunderstand about a collected look. We hear “not trying” and assume it means throwing things together and hoping for the best. It doesn’t. Lauren has talked about wanting everything he makes, the clothes, the decor to carry that natural, easy feeling, and he’s been honest that achieving that ease is its own kind of work. The effort is real. It’s just supposed to be invisible by the time anyone sees the result.
I feel this every time I walk into my own living room. The French Brides box on the shelf didn’t get there because it “worked with the palette.” It got there because Steve and I hauled it back from Round Top. I couldn’t imagine the room without it now. The vintage wicker travelers trunk doesn’t match the modern coffee table or the sofa in any textbook sense, it’s just good, and somehow I think that’s what makes the whole room hang together instead of falling apart. The wicker echos’s the colors of the antique baskets, vintage juggling pins, and the antique document box.
That’s the paradox of collected style: it looks effortless specifically because the effort went somewhere you can’t see it. Mine started over thirty years ago, antiquing in Maine, when we bought a corner cupboard with two doors missing, beautiful patina and butterfly shelves. We’ve moved that cupboard through three different homes since, three completely different collections, three different color palettes, and it has never once looked out of place. A brand-new piece could never do that. It hasn’t lived long enough to know how to belong anywhere yet.
It’s why I’ve always loved vintage more than anything new. A brand-new anything is still trying, the finish is too even, the color too uniform, the whole object still auditioning for your approval. But something old has already stopped trying. The paint is worn where a hundred hands touched it before yours. The linen has softened into a color that no dye lot could ever quite replicate. That imperfection isn’t a flaw, it’s the entire point. It’s proof that the object lived a life before it met me, and that’s a kind of honesty no perfect, pristine thing can offer. The art isn’t in finding something flawless. The art is in the flaw.
Lauren himself proves this in his own market. Vintage Polo and RRL pieces from his current collections are some of the most collectible things he’s ever made, and it’s not despite the wear, it’s because of it. A faded flannel (ralph himself said one of his favorites came from K-mart) or a broken-in field jacket is worth more to collectors precisely because it looks like it’s already lived a life. He built a business on things that look easy, and the ultimate expression of that ease turns out to be age itself.
Fashion victim vs. your own monogram
Lauren has warned for decades against what he calls looking like a costume, dressing so hard at a trend that you disappear into it rather than showing up as yourself. I’d call that the opposite of wearing your own monogram. A woman who is trying too hard to look current is, perhaps, the least memorable person in the room. The ones who actually stop you, who make you want to ask where they got that scarf, are almost always wearing something slightly imperfect, slightly worn, entirely theirs.
This is the real argument for the collected wardrobe over the fast-fashion cycle, and it’s not just an aesthetic preference, it’s almost a philosophical one. Fast fashion asks you to try constantly: try to keep up, try to look current, try to guess what’s next. A collected wardrobe asks you to do the opposite. Buy the linen blazer because you love it, not because it’s “what’s trending” or some fashion influencer tells you you have to have it. Wear it until it’s soft. Let it become the thing you reach for without thinking, the way Lauren’s own signature pieces, the white shirt with the sleeves shoved up, the jeans worn in at the knee, the jacket a size too big, all read as alive precisely because they look lived-in rather than just-bought.
Don’t be afraid to own your own style after 50 and beyond with confidence.
What effortless style after 60 actually looks like
In my closet, not-trying means I’ve stopped asking “does this go with that” and started asking “do I love this.” Those are different questions with different answers. The first one keeps you anxious and shopping. The second one, over enough years, builds you a wardrobe where almost everything goes together, not because you planned it, but because it all passed through the same filter of genuine affection. This is the same idea behind my collected wardrobe piece how to build a personal style that tells your story. where the through-line across a room or an outfit isn’t color or trend, it’s feeling.
In the house, it means I just let things be a little wrong. The garden roses go in whatever pitcher is closest, not the “correct” vase. Scout’s bed sits in the corner of the livingroom in full view of guests, because pretending we don’t have a dog who lives here would be its own kind of costume. My tables have a collected look rather than perfectly styled.
The chapter you’ve earned doesn’t need to prove anything
There’s an age element to this too, and I think it’s the part that matters most. Trying too hard, with your clothes, your home, your face, any of it, is often, underneath, a kind of apology. It says: I know I’m supposed to look a certain way, and I’m working on it. Not-trying, real not-trying, is the opposite stance entirely. It says: this is what I love, this is who I am at seventy, and I’ve stopped auditioning.
That’s not a resignation. It’s the reward for paying attention for decades. By now I know which roses I love, which fabrics feel like me, which chair I’ll never get rid of. The knowing is the effort. The ease is what you get to keep once the knowing is done.
So the next time a room or an outfit feels like it’s trying too hard, ask what it’s trying to prove, and to whom. Effortless style after 60 isn’t the absence of effort. It’s effort that is old, genuine and yours alone. Own your own style. How do you feel about this concept agree or disagree?
Great post today! I’ve always wanted to be different than anyone else….so I like vintage and antique and my way of putting outfits together. The problem is when you get asked where did you get that? I can’t name a store for you to go purchase what I’ve got or wearing.
Hi Nancy
Ha! I totally understand what you are saying! I have the same problem quite often!
Hi Cindy,
As usual you share so many excellent topics. It gets you thinking what you communicate and then you engage us to think about how it applies to us. I like this very much.
I’ve read that people dress the way their home looks. I have found this is not always true. However I find it interesting if your home is styled super well (whatever that is) but you have issues putting yourself together! No judgement at all, I find this topic interesting.
When I see your home and the way you dress and with the fabulous accessories, you match your home AND you do both so well.
Ralph Lauren is fabulous, too bad I donated so many of my clothes many years back. Oh well, hopefully found a home that was able to re-love the items.
Thx for a thoughtful post. You always put your whole heart ❤️ into everything you do, say, and share.
In appreciation .
Hi Katherine
We can’t keep everything can we? I wish I had saved more of my RL country things. They are so collectible now!
Excellent article!
I saw your bag in the Paris article too. Is it the nylon or leather bag? I am off to Ireland and need a new bag. Please share as I could not tell from the pictures.
Denise:)
Hi Denise
It is nylon. It is a great travel bag!!
Thank you for this post! I love RL and his take on Americana. It is idealistic and I have a picture of my mother in the Depression on a family farm wearing what is now ‘cool’ overalls and boots..not an outfit to lounge but one to milk cows and walk in mud. His dreams of the ideal life and nostalgia in the past are curated to remove the problems of poverty and hunger on one hand and the grand mansions on the other. That’s OK because he recreates it beautifully…we can forgive that because there will never be another RL! I loved wearing his clothing in the 80s and wish I had kept some of it..the lace blouses and the elegant, long skirts that return in fashion time and again. Thank you for reminding me.
I love everything in your home!! and I love how everything tells the story that’s just how I think it should be!! and I think you have a perfect effortless style.
Hi Martha
I love your charming home and style as well. You dress like your home and vice versa. You have it all figured out!!
AMEN! Can’t think of any ways to say it better! I’m am sick and tired of the picture perfect rooms that no one lives in (and frequently in many instances look identical) and the fast, cheap fashion industry. At this point (64) everything in our downsized home and my closet has to be useful or make me smile….usually both.
Hi Renee
I couldn’t agree more! Our kids have always appreciated the old and new and have a mix in their own homes. We will be downsizing at some point and will put a lot in storage. My daughter has a very small house now but would love some of our pieces when she adds on!
What an absolutely beautiful post. Both your words and images dig deep into thoughtfulness and challenge us to look around and consider what we’re projecting to the world. I’m genuinely inspired to walk through my home — and even my closet — with a wiser, more intentional eye.
You never disappoint, Cindy.
Hi Holly
You inspire me too with your courage and thoughtfulness.
Amen! Buy it because you love it and it calls your name. Use it to death
Absolutely!!
This post totally resonated with me today! I find myself reaching for the same few pieces this summer over and over for different occasions. Maybe at 74 I’ve finally “embraced “ my style.
On the home front I love watching people wander around our home and cottage and have them ask questions about various pieces. I heard Nate Berkus say that your home should tell your story and yours certainly does.
Beautiful!
Hi Barb
I love Nate Berkus and his style. Our homes and our wardrobes should tell our own unique stories. I shared a story on IG today that someone wrote about the Olsen sisters style (the Row) comes from inspiration from older women. Their style is very classic. I love that!!
Does the expression “ matchy matchy” ring true in this case? I hope that by the time most of us have hit this age, we have figured out what best fits for us, both in our clothing and how we are comfortable in our living spaces. Thanks for reminding us about these things and also, not to dress to impress…..wear what makes you feel good!
Hi Wren
That is why we are pals!!
Great post today Cindy! I agree with everything you said.
Hi Cathy
I wasn’t sure when I penned this post if you all would find it interesting or “bleh”. I am so glad you enjoyed it!
Thank you for your post. I always love seeing photos of your gorgeous home and gardens. I’m going to try to remember that phrase “the art is in the flaw.”
Hi Karyn
I have always been attracted to the worn and imperfect for as long as I can remember.
Lovely post. You definitely own your own style and it’s great.
Hi Mary Ann
You have such great style and you are such a great entertainer!! You and Howard are an amazing team!
I read your interesting post and then fell down the rabbit hole of linked posts. Lots to think about. Makes me want to go dig in my closet and play with my accessories. I do not wear them nearly enough. Love the photo of you wearing a shirt with pins floating down the center.
Thanks for inspiring me.
Hi PJ
You ladies inspire me to be creative because you all lead such full interesting lives. I can’t be a “straggler” when I am surrounded by suh inspiring people!!
Thank you for giving me faith in my own home. My husband and I married late in life after losing our long term beloved spouses. We have a somewhat mixed “look” as our home includes many pieces gathered from long ago travels to different places. We have kept those that have real meaning, and added newly acquired bits as well. It turns out to be a home of great memories and comfort to both of us, with lots of stories to tell.
Hi Sharon
I love that you have combined your treasures and you both enjoy them so much. And how lovely that you found one another late in life.
Great blog post! I am redoing a condo on a smallish budget, and Facebook Marketplace is excellent (in a large place like the Bay Area). Reuse, recycle and fun to thrift “unique” items! Lots of slightly used items
in excellent shape. And LUUG here in the Bay Area a reasonably priced moving service. Also NIXXIT in the
Bay Area: a woman owned reasonably price service to haul away stuff.
Hi Mary
Thanks for all the tips!!
Soooooo pretty
Thank you Rory!!