How To Wear Sneakers When You Are Over 50. Or 60. Or 70!!

Sneakers.  So much has been written about them over the years.  And sneaker styles have changed over the decades.  I’m gonna bet that if you are a regular reader of this blog you wore P.F. Flyers when you were a child.

Watch this carefully because they weren’t even called sneakers. They were called “Canvas Shoes”.   

Or Keds.

Keds have pretty-much remained the same, but these days, I like a thicker sole–the one in the middle is my choice. I like the way it can blend into a wardrobe.

They have been praised for comfort and dissed for lack of fashion and style.  Come on now.  How many articles have you seen about not wearing sneakers to European cities for fear of looking like a tourist?

And I have to say,  we Americans can look a bit too casual when we visit European cities. I’ve seen worse than this in Paris. And if you take the time out to look for a good-looking and comfortable sneaker or street shoe, you CAN find something very flattering!

But—it depends on the style of sneaker that’ll make or break a look.

Going back to my “mom” days in the 90’s, my summer footwear consisted of either flip-flops or those leather classic-style Keds.  And I wore the Kids only with shorts because they looked better!  Add to that I was always traipsing through baseball fields, soccer fields, and outdoor Irish Dance competitions—canvas would have gotten filthy.

I’m not kidding. THESE were my go-to’s for sports events, running errands and just being mom!  And the leather was a more pragmatic choice because it cleaned easier. And they always looked good.

And as I aged, I noticed something.  There was a stereotype sneaker for the more mature and pro-aging woman.  Now please realize something.  For those who need orthopedic sneakers and shoes—I completely understand—but this post is more of a style one.  So, I’m not dissing anyone or shaming.

This particular sneaker is marketed toward seniors—and not the seniors in high school.  They are marketed to the over 60 crowd and I think it’s absolutely horrible.  Not all of us prefer or want to wear those clunky, Velcro shiny white articles of footwear.

This sneaker is actually marketed for “senior citizens”. It’s hideous.  If I was a nurse working in a hospital I would wear these at work and that’s it.  Velcro?  Velcro?  What?  We can’t tie a lace when we are over 50? 

We want our sneakers to be as hip and cool as we are!! Let’s hope that marketers and advertising people for once, start to include the pro-aging demographic in their ads.  And moving on to how to wear sneakers….with a modern vibe….

For me, the most versatile sneakers are Chuck Taylor Shoreline low tops by Converse.  I’m a very lazy woman and therefore don’t like to tie my sneakers in a bow.  I prefer the little knots in the laces as shown in the pic below. And these sneakers slide right on, making them even better for the laziest of the lazy!

I LOVE these sneakers. And for those who may not be able to bend down to tie a lace, these slide on.  The back is elastized and still remains pleasing to the eye!

Image result for chuck taylor shoreline white sneaker

The elasticized back is perfect for sliding these babies on and off!

Like how I made the laces lazy-friendly?  Me too!

I also like the traditional boat sneaker.   With both, the thicker sole gives a nice finished look with summer clothing and is more in proportion with how you wear them.

I love a good boat sneaker too.  I’m more of a streamlined person. Very basic. No bells and whistles..

I dig these too. In fact, I think I’ll buy a pair.

With jeans, I like to fold the cuff up a bit. It gives a fun and casual vibe that we all strive for.

True dat. I’m a sucker for cuffed jeans with sneakers!

The trend with sneakers and dresses is also a fun one—but beware. Not all dresses were meant for that sneaker/dress combo.

This young woman nailed the sneaker/dress look. AND, this is a very “mature” woman ensemble!  The sneakers are ever-so-slightly-thicker without being downright clunky looking and that dress.  Yeah.  I love this look!

A short skirt/sneaker team is one of the best for a fun summer look and the more casual, the better.   A casual dress also makes for a great pairing.

A maxi/sneaker look can be just fine but you need to keep things in proportion.  A too-long maxi looks better with a higher heeled sandal—but a maxi that cuts above the ankle is great!

Let’s look a bit more—shall we?

Here’s the cuffed-jeans/sneaker look.  I don’t wear jeans much in the summer due to the heat and my seat sweats so I don’t want to be stinkin’ like a swamp if you get my drift. But during the cooler months, I love this casual look!

A rather elegant look with my bra straps hanging out–don’tja think?  Actually, I like this knit maxi with sneakers because the dress is just so basic and….

….the hemline falls just above the ankle.  Anything longer I wear with sandals.

This Lacoste polo shirtdress is a GREAT match for sneakers.  It’s got a fun vibe…and yes, you CAN wear a mini when you are over 50!

Fabric is a factor.  A flowing material or knit works better with a sneaker–it’s more casual-friendly…

A white tee + a flowy skirt + sneakers = a winning combination

An exception to that fabric rule is denim.  A demin skirt and sneakers were meant to be worn together!

I don’t even remember when I bought this skirt but I love the movement and the polka dots!

When I tried this dress on at J. Crew Factory last year, I was wearing these sneakers.  I loved the look so much that I purchased the dress–and nine out of ten times, I wear this dress with those sneaks.

More dressing room looks.  I tried this dress on earlier today and passed because of the fit on top–but I love the way it looks with the sneakers.  The pants.  I cuffed the hem as shown in the photo with the striped shirt.  That was the win. And I purchased them! I’m really pissed about that dress though because I really did love it!

And the shorts!  For me, again–it’s proportion. I don’t like my shorts to be long because I don’t have long legs.  Long shorts on short legs can look squat.  A shorter pair of shorts can make your legs appear longer–but that means you have to shave your entire leg. And I’m a fan of the sneaker/short combo. It’s a nice crisp look..

This is what I’m wearing now.  A classic summer look…and..

…it can be dressed up a bit with a blazer. I wore this ensemble shopping today. And let me tell you this is a very fun look for we women over 50 and 60 and upwards!

Even with a dressier pair of shorts–sneakers can work….

This is a look that I wore to work but I’m telling you–we’re going to NYC for a weekend next month and I’ll bring this ensemble along–and I will wear my sneakers instead of the heels because it’ll be a great city look!


I also want to point something out.  I’m bowl-legged.  The thing is, I know how to position my legs when I take photos.  My knees are also knocked and I’ve got crepey skin but it doesn’t stop me from wearing all the above-combinations.  We’re aging.  But we need to be PRO-aging and not let the veins or the discoloration or the crepey skin keep us from wearing what we want.  You can wear sneakers and rock on!

I created an idea list on my Amazon page  for you to look at.  Take a look at some of the dresses and sneakers and make a mental image of what you like–then when you go shopping, you’ll have a visual of the look you are going for!   HOW TO WEAR SNEAKERS

Elvis. Hi Heel Sneakers. Is there anything else?



About Catherine

Far from perfect, but enjoying life as a non-perfect and flawed individual at 60 years young. I'm still wondering what I'll be when I grow up! The characters in my life's screenplay include my better half. He is a refined Frenchman who grew up in Paris and summered in St. Tropez. I grew up in Long Island and summered in Long Island. I am not refined. My three grown children are also a big part of my life. For their sake, they happily live where their careers have taken them! But I can still mother them from a distance! I write about the mundane. I write about deeply shallow issues. But whatever I write or muse about--it'll always be a bit on the humorous and positive side! It's all good!
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30 Responses to How To Wear Sneakers When You Are Over 50. Or 60. Or 70!!

  1. hipchick66 says:

    When I was a kid, all we had were Chucks or Bobos (the little white canvas sneaks). These days, as much as I’ve tried, Chucks just don’t fit me right (except for the one pair of charcoal Dainty Chucks I have) and Keds always cut into my ankle. Instead I wear Skechers or Danskin. But I love seeing others rock their Chucks!

    • Catherine says:

      Hi Lori! I never heard of Bobos. Were they a Philly thing? Chucks remain one of my faves. I have been wearing them on and off for years. Some years I’ll wear them and then some years I won’t. I have a black pair somewhere in the garage–that is if Bonaparte hasn’t thrown them out!!! XOXOXOXO!!!

  2. Juliet says:

    Oh what a timely post – I have terrible legs, but you know we have the absolute right to wear what we like and to look good. A good trainer/sneaker/sandshoe – whatever makes all the difference. Currently I love my navy gazelles and my grey campers = the campers knits instead of laces your tie – like yours, they have a cute wee zip ip the back and are a great brand. For me, having comfortable feet are the basis of anything – your feet hurt – it shoes in your face and everything hurts, you cant look good if you are wincing with squashed feet!!! And I think sneakers/trainers are very older woman friendly – we can really rock this look (as you aptly prove in your photos), this isnt about competing with out age groups – this is a look we can own!!!

    • Juliet says:

      sodding autocorrect, my english is now mince. The campers have wee knots – instead of tying in a bow. Dont know how autocorrect corrected me into a new language – but a wee zip “ip the back” sounds a bit like my kiwi accent is being typed there…

      • Catherine says:

        OMG. Juliet. Don’t even get me started on the autocorrect. I can’t stand it!! But it’s so true. We can own the sneaker look if we do it right. And I like what you said about us not competing with other age groups. That’s very pragmatic!!!! Something that I am not!!! LOL!!! XOXOXOXO!!!

  3. You rock the sneakers like no other! Love them with those dresses; you look awesome!

  4. Catherine, I love your Chuck’s! How do you keep them looking so good? Anytime I wear a white sneaker they immediately start to look less than pristine! I love my Keds, but I am still looking for a pair of Converse that don’t make my feet look like skis. Ha, ha. Yours look very cute and I love all the outfits you paired them with. – Amy

    • Catherine says:

      Hi Amy! It’s the style of the Converse Shoreline. They don’t make your feet look like boats and that’s the one ding about the other Chucks–they make you feet look larger. These ones are perfect. And with the white sneaks. I’m just careful with them. When they get grungy looking, I’ll throw them in the washing machine. That’s what I did when the kids were younger I put the white canvas sneakers in the washing machine and added a bit of Lestoil to the detergent. Never in the dryer though. AIR DRY only!!! XOXOXOXO!!!

  5. Miss Bougie says:

    I totally agree. I wear sneakers a lot, especially with jeans. I don’t like the clunky ones, they make my feet look massive, especially when they’re white. I wear Geox Snake or Vega models. I don’t even need to try them on at the store they fit like a glove. So comfortable! I have started buying them over the internet.
    I like how you look when you pair them with shorts.

    • Catherine says:

      Hey B. Yeah. I love the look of sneakers with shorts too. And even though I prefer a thicker soled sneaker, I don’t like the super clunky ones–not attractive at all!!! XOXOXO!!!

  6. Lise says:

    I really love your outfits with sneakers. Unfortunately I have yet to find a lace-up sneaker that does not hurt my toes. The slip-ons are a bit better. Have no idea why, I don’t have such unusual feet. Maybe I need to try leather ones. Just don’t want to spend a lot and then find I cannot wear them.

    • Catherine says:

      HI Lise! Itsn’t it odd how certain shoes just don’t fit our feet correctly? I love the wedged shoes but for the life of me cannot wear them. My instep is naturally too high and the wedges just don’t work. Fortunately for you there’s a good number of slip on style sneakers that are nice!!! XOXOXOXO!!!!

  7. Bobbi says:

    A friend turned me on to Allbirds. I have 3 pair now, a tie and 2 slides. They’re wonderful for aging feet and the first shoes I can wear comfortably that aren’t Birkenstocks or with my orthotics. I can wear them without socks and that’s unusual for me in a closed shoe.
    They’re all wool, nothing to bother my crooked toes, and washable. The insole is wool and can be replaced. They have a new model, also washable, I’m getting next, made from another sustainable fiber.

    • Catherine says:

      Hi Bobbi. I just went on to the Allbirds site and I love the slipons!!! The price isn’t inexpensive but since they are sustainable and from what you said, super comfortable, I’ll bet they are worth every penny. This brand will be on my watchlist for sales because those slip ons are really nice looking. In fact, I’m going to tell Oona about them because she is going to Italy for a couple of weeks at the end of the summer and will be walking all over the countryside!! Thank you so much for that link!!!!! XOXOXOXO!!!

      • Bobbi says:

        We have a Half of Half store near us. They had them for about $25.00 at the Kansas store twice. Probably overstocks.
        I agree they would be great for Europe. When we go shoes take up too much of my suitcase because of my skinny touchy feet and they pack great. I only wear the ties to Tai Chi, the slides are more comfortable to me, even in the 90 degree Kansas heat.

    • Beverly says:

      Merinos is also an all wool sneaker. Lace up and slip on and not nearly as expensive. They fit the same, too. They feel like you’re barefoot.

      • June says:

        For me, new sneakers always remind me of going back to school and the excitement of another new year. My mother always wanted me to wear a new boat keds sneakers for gym as she thought they conveyed some king of status. Tennis, sailing, etc. She skimped on a lot of things and even made a lot of our clothes but she always paid for high quality sneakers. Any one else associate new sneakers with going back to school?

  8. vavashagwell says:

    I’m a shoe person and so immediately had to open your blog post. Love your outfits with your sneaks! I have several types of sneakers, one being some Chuck high tops covered in silver sequins. They seem a bit room with my narrowish foot but I wear them anyway. The only Kate Spade item I have is a pair of Keds in royal blue glitter, those will be out on the Fourth of July. I also like your attitude about aging. Sure, we may not have the legs of a 20 year old, but we can still wear shorts! I wear shorts all summer long, now that I’ve been retired. It’s one of the best parts of summer!!!

    • Catherine says:

      Hi Vava! Those Kate Spade Keds sound like a great and fun pair of July Fourth sneakers!! The Chucks—listen, these Shoreline sneakers that I have are very narrow-feet friendly. I think I sized down too. They are really comfortable too.
      Oh…hell yeah–my legs are bruised from all the bumping into things that I do and cut and full of nicks because I don’t take my time shaving my legs…they are aged and I don’t care because during the summer, I want to be cool as a cucumber and very comfy. Jeans are just too heavy for me this time of year!!! I’m with you!!!!!!!! XOXOXOXO!!!

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  10. Marie says:

    Really liked this!! Good work.👍 Just purchased 2 pairs of Converse sneakers last week and intend to wear them alot. 😉

  11. June says:

    I love your outfits with Chucks. I too love a clean boat shoe with a thicker sole. The traditional navy or white styles are so classic. Keep them clean however. Just can’t stand the ugliness of the running shoes that so many women choose to wear. They look like clodhoppers. I’ll take a clean Keds or Sperry boat sneaker any day.

  12. Martha says:

    I have a pair of navy blue converse with double tongues — if i fold down the blue tongue, underneath is a purple tongue! Just so happens those r my 2 fav colors 2 wear….SCORE!! 🙂 BTW, i am 57 and do NOT wear shorts out of the house— i feel my best in jeans, a long sleeve buttonn-down, a baseball hat and of course my converse sneakers….

  13. Patricia Clark says:

    where are any pictures of really OLD ( like 90) women wearing Converse tennis shoes

  14. Marl says:

    Great article for us aging crowd! Lots of choices and idea’s.
    Thank you!

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