Pleated Shorts For Over 50 Women

Happy Monday ladies. Let’s talk about pleated shorts for over 50 women. Do you wear them? I seldom do. I wore them when I was younger but less and less in my late 20s, and by my mid-30s, I didn’t own any. Let’s face it, I’m not alone in my avoidance of shorts. Many women simply don’t feel comfortable wearing them for a multitude of reasons.

Today I’m joining Susan at une femme d’un certain âge, Tania at 50 Is Not Old, and Deborah at Fabulous After 40 to share how we style shorts.


woman wearing navy linen shorts and white denim jacket

In order to pull this off, I started with the most important thing… a tube of my favorite self-tanner. My pasty white legs are always helped by a tiny bit of color which hides some spider veins and takes away that blue tinge:) I use the “fair to medium” natural glow version which builds very slowly and never leaves orange streaks.


over 50 blogger wearing navy shorts with white sneakers and striped tee


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Shorts are a very sporty look which certainly fits my lifestyle but not my style aesthetic so I’m styling a cuffed and pleated pair that feels a bit more elevated and resembles a skirt from a distance. These shorts have a 5 1/2″ inseam which isn’t long enough to be considered a Bermuda short, but the slant pockets, belt loops, and cuffs keep them from resembling gym shorts.


blonde woman sitting on wall wearing white denim jacket and striped tee

What is the most flattering length shorts for over 50 women? The ones you feel confident wearing. The skin above our knees sags along with many other body parts as we age, so the most flattering length for you is a personal preference. The shorter the shorts, the longer your legs look, but there is a limit and each woman knows her own:)



blond women over 60 wearing striped tee and navy belted shorts

These shorts are a linen/rayon blend with a high rise and are available in 3 colors sizes XXS – XL. Pleated pants and shorts have a tendency to look very full in front so be sure you balance fit with fullness. I’m wearing a small. My shoulders are broad, so pleated shorts help balance my figure and keep me from looking top-heavy.


jennifer of a well styled life wearign navy pleated shorts and rothy's sneakers

I tied the sash off center but you could easily remove it and wear your tee or top over the waistband. My straight figure needs as much waist definition as possible so I tucked my navy and white striped tee in to keep me from looking blocky. These shorts also come in several different stripes, but they felt overpowering on my short legs so prefer the stripe on top and solid shorts on the bottom.


woman wearign whte denim jacket, navy pleated shorts and white sneakers

I’m loving bright white sneakers this season but they do lose some of their charms when they get scuffed and dirty. I was thrilled to find these Rothy’s lace-ups which will always be clean! Rothy’s uses plastic bottles and marine plastic to create a signature thread which they use to make all of their shoes. They’re totally machine washable, and very durable so will look crisp all summer. They are available in 5 colors and 3 two-tone, sizes 5-13. They’re only available in whole sizes so if you’re between, order up. They will give a little but they do not stretch out.


over 50 woman wearing pleated shorts and denim jacket

Now let’s pop over and see how Susan at une femme d’un certain âge, Tania at 50 Is Not Old, and Deborah at Fabulous After 40 style their shorts.

Are you a shorts wearer? What’s your favorite length?

Thanks for reading ladies and remember to wear what makes you feel confident.




  1. Hi Jennifer.
    I love how you put clothes together.
    Last year I bought a few skorts at Costco and have only worn them once. Still trying to adjust to my 68 year young body. 😂 I find skorts are a little more flattering than shorts. Could you recommend a self tanner?

    1. I’m a big fan of the one by Jergens. It never streaks on me. I apply every third day after my shower

  2. Living in the Pacific Northwest, I do not wear shorts much. I prefer a summer skirt or crops. Once in a while if it is a really hot day I will wear shorts at home. I prefer the longer length shorts.

  3. I have great legs (hey, it’s all about confidence, right?) so I do wear shorts and skirts a lot. I like shorts with stretch in them so I can move easily. Shorts are good for casual outings, but I would never wear them to a restaurant, theatre or going out anywhere.

    I just watched your latest Insta discussion – a couple of comments:
    – I really hope there will be a return to dressing up on occasion.
    – I too hate barrel pants!
    – I’m also over skinny jeans. I still have them and wear them, but I’m on the hunt for straight leg pants!
    – Love palazzo pants, but you have to wear them with heels, IMO.

    Really glad you and your colleagues are doing these weekly videos!

  4. Your outfit looks so very cute on you.
    I wear shorts around the house but wear longer shorts or Capri length pants because
    I feel more comfortable when I go out.
    I do use a self tanner which helps the ghost white leg situation. Also had vein injection therapy last year which improved my legs a bit.
    Still feel more comfortable with longer length shorts.

      1. I had injections for spider veins behind my left knee and a few on the side of my knee. The injections made them disappear so very happy about that. Lately small ones crop up every so often but aren’t very noticeable. Cost me $700 out of pocket which took me awhile to pay off but I’m happy with the results. I’m 70 and I still wear shorts out in the yard, to the store, and to go for walks. I forget my age; I feel like I’m still 50 so I still dress like I’m much younger and people think I’m actually in my 50’s. Maybe because I’ve been raising my 13 year old granddaughter for 10 years 😊. Anyway Jennifer, the shorts look great on you. Actually, everything you wear does!

      2. Thank you for sharing. I know my mom had her’s “stripped” many, many years ago which sounds barbaric. I’ll ask my derm about injecting the one that’s starting to bulge on the back of my leg.

  5. Dresses are cooler, IMO. Shorts just air out the calves, but that uncomfortable “upper” warmth continues in tightly fitted short pants. Those fuller leg shorts in the picture would be better, but my shorts-wearing days are over.

  6. This is another great look on you, Jennifer! I find the only way to determine if shorts are going to be flattering is to try every style, every brand, in every size. I tend to like the softer materials with a short zipper or elastic waistband, that won’t bulge or cling. And yes, as I’ve mentioned before, skorts are a woman’s best bet in summer months! P.S. Even when I was younger, I just don’t know how women look good in khaki shorts!?!?! lol

  7. Pleated!!! Big NO on that. Pleated fronts look poufy – a look I don’t want. I wear slim fitting bermudas that end right above my knee. Very slimming look. Self tanner is too much work. I don’t care how white my legs are.

  8. I live in shorts all summer! Usually Jean shorts as I work in my yard a lot. My favorite style was about 10 years ago that were a little looser on the leg and about 7” long. I quit buying new ones when they started making them tighter in the leg. Since I am only 5’2” I can’t wear Bermudas. I am 72 and my legs are not as nice as they used to be, but I don’t care. My mom still wore hers when she was in her 80’s in assisted living.
    Jennifer you look great in shorts!

    1. Mary Lou, check out Old Navy. They make very nice affordable cotton shorts with a sense inch inseam. The fit is flattering and they are not too tight fitting in the legs!

    2. Hi, I just cut off a pair of old jeans that I haven’t worn in a while. They make great gardening shorts. Of course, it would help if I cut straighter! Tip from sewing friend: make back legs longer.

  9. These look cute on you and I love that waist tie style but I tend to avoid it as I carry my weight in my tummy. I like the idea of the white jean jacket with them. I think I will try that with my black Bermuda shorts. Cheers, Deborah

  10. Like others have mentioned, I too, wear skorts rather then shorts. I like the way they hang over my belly rather than hugging it as shorts do. I can even wear them and still do Tai Chi so I can easily go from my class to shopping or casual lunch with a friend. If I try on shorts I’m definitely more aware of my legs than I am in skorts. I still have nicely shaped legs, but they are aging legs and they don’t seem as exposed in a skort.

  11. If I didn’t know better, I would swear you read into my thoughts sometimes …. lol! As just yesterday, while going through my closet I came across the only pair of shorts I currently own which are classic in cut, have a ten inch inner seam with a plain front that I haven’t worn in years. I did try them on and regardless they still fit well, I am still not sold on wearing such however will have to give them another shot as wasn’t concentrating too much on how I was styling them. With that said; yours look great on you and thanks for the inspiration. -Brenda-
    P.S.: I have a button-front shirt dress on order that I planned to also wear with just below-the-calf leggings buttoned down to the waistline (or as a 1st piece overlay) so perhaps will experiment wearing the shorts under it as well, to ease me into a comfort zone of wearing them.

  12. Love this look on you Jennifer!
    I seem to have some crazy internal alarm that steers me clear of certain clothing options and one of those is shorts. I have found enough other choices to wear in the heat and humidity. I guess you don’t get to a certain age without developing a personal style that you can live with comfortably.

  13. Yes I do wear shirts but a bit longer. My legs are longer than my torso so 7 inch (9 sometimes ) inseam look best on me. I also use a fair -medium self tanner on legs and arms (occasionally) in summer. I’ve spent the last four days by the ocean so I wanted to dress sporty as folks who live here do—all year!

  14. You look great in your shorts. I rarely wear them. Really only on the golf course but even then I wear golf skirts because they are a little longer. I like wearing workout capris.

  15. I rarely purchase shorts anymore but I do find the need to wear them during the summer. I prefer bermuda length shorts and ones with a slim, flat front. The last thing I need is more fullness in the front! So I will not be buying any pleated front shorts.

  16. The outfit is so fresh looking, I love it on you! I have to many scars, so Bermudas or longer for me.

  17. Look at you, you skinny-minnie. I couldn’t wear pleated shorts if I tried because I carry my weight in my stomach region. However, you look fabulous in this entire outfit!

  18. You look good in the shorts. After bicycle accidents, scars and added years I wear the only while working in the yard o wet tent camping, and only then if the bugs and brush are not bad.

  19. You look terrific in these shorts! I haven’t worn pleated anything in many years.

    The only shorts I’ve managed to wear have been an A line – knit shorts with a length closer to my knee and the furthest I’ve gone with them is my front lawn.

    But I do like skorts and by googling “knee length skort” I found a great one on Amazon for under $30.

  20. You look very fresh and sporty, Jennifer. Like you, my “eye” has a hard time adjusting to seeing myself in shorts.

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