Shorts For Women Over 50 : A Dressing Room Review

I don’t wear shorts often, but I know many of you do, so I’ve been trying on several brands to get a feel for what’s out there. I thought it would also be helpful to include some styling tools to help you wear shorts over 50 in the most flattering way this summer.

If you’re new here, welcome. A dressing room diary is when I go into a local store for a try-on session so you can see what’s new and how it looks on a woman over 25. For reference, I am 5’4″ and weigh around 142 lbs. I have broad shoulders with straight hips, a long torso, and long arms. I often buy one size larger on top. You’ll see me try on clothes in colors and shapes that may or may not flatter me because I want you to see what’s in the stores and get some styling ideas. I tell you what sizes I am wearing to help you understand how things run.

Talbots Shorts For Women Over 50


I’m seeing lots of longer, Bermuda-length shorts on the racks these days. They’re great for women who want some extra leg vein or loose skin coverage. Longer shorts can easily be dressed up and worn with a small wedge or heel. These polished shorts are a cotton/spandex blend and come in eleven colors. They’re made from a stretch cotton twill with belt loops and front slash pockets.


These are the “perfect” shorts in navy and white gingham in petite with a 9 1/2″ inseam. I prefer this slightly shorter length on myself. The more leg you see, the longer your legs will appear.


These relaxed chino shorts are in a fresh blue and white 100% cotton seersucker. They have a 7″ inseam in regular and plus and a 6″ inseam in petite. They have a fly and button closure and front slash pockets. Seersucker is such a classic summer fabric it looks great in shorts.


These twill shorts have a causal vibe in a cotton/lyocell/linen blend. This pull-on style comes in 3 colors. The inseam is 6″ in regular and plus and 5″ in petite.

Styling tip – The shorter the inseam, the flatter your shoe should be. Nude or pale-colored sandals and wedges help elongate your leg. The longer the shorts, the more chopped and short your legs will look.

Ann Taylor Shorts


These pleated shorts are a fully lined linen/rayon blend. The belt is made from braided fabric. This regular has a 6″ inseam, and the petite has a 5″ inseam.

Styling tip – Pleated shorts have a wider leg opening which can be more forgiving for ladies with thicker thighs. If you have very thin legs, you may prefer to avoid these because they’ll highlight how narrow your legs are. Pleated shorts are fun to dress up with a lightweight blazer and wedges for a more elevated look.


These boardwalk shorts come in curvy or regular (straight) and regular and petite length. They’re in polished cotton with 3% spandex. They come in four colors, sizes 00-18. The inseam is 11″ in regular and 10″ in petite.

Nordstrom Shorts

pleated shorts shown on woman over 50

These linen/viscose/spandex shorts have a 9″ inseam and a loose, flowy fit. They’re available in four colors, sizes 00-16.

Styling tip – These classy-looking shorts could easily be worn to work, church, or dressier events. I’d add a narrow belt, simple jewelry, and a small crossbody bag. Wider shorts like this need a narrower, shorter top for balance.

Wit & Wisdom Shorts


These shorts are a cotton/polyester/rayon/spandex blend with jeans styling and an unrolled inseam of 9″. They come in six colors, sizes 24-34.

Styling tip – Cuffs on pants shorten the look of your leg, and it’s even more true with shorts.

women showing two ways to wear top with long shorts

These Wit and Wisdom shorts are a very soft denim cotton blend with plenty of stretch. They have a 15″ inseam and come in sizes 24-34. The cuff would easily fold up several more times to adjust the length to your liking. While I almost always prefer tops tucked in, I prefer this one untucked so the top and shorts don’t appear the same length. A 50/50 split is never as pleasing as 1/3-2/3.

NYDJ Shorts

women wearing below knee shorts

I thought these were long shorts when I grabbed them from the rack but discovered that at my height, they look more like pedal pushers. They have a 13″ inseam, which on me, are not shorts. They have a slit on the outside of the hem, so you can’t roll these up easily. If you’re nice and tall or like the below-knee look, they’re terrific.

Chico’s Shorts For Women Over 50

woman walking at shopping center weagn white shorts and denim shirt

Chico’s make the same shorts year after year. These Brigitte So-Slimming 10″ shorts from 2021 are the exact ones they’re selling today. They come in tons of colors, are super easy to care for and have plenty of stretch.

Where do you like to buy your shorts?


  1. I appreciate seeing how shorts look on another woman my age. I am very short waisted so tucking tops in doesn’t work for me unless I blouse them quite a bit or, when they were available, I would by low waisted pants/jeans. Otherwise I look really silly with my shorts riding around my rib cage. 1/4 to 3/4 ratio is not flattering. Just a word of caution to my short-waisted friends.

  2. So happy to have found your blog! We share similar style, shape, weight and coloring, though my hair is darker. Its easy to see if I will like something by you modeling options. Love that you give size specifics as it really helps with online ordering. Also, thank you for turning me on to Nordstrom! I only have a Rack near me. The free shipping and returns is awesome! My only problem is since finding you, I’ve been spending a lot more money!

    1. Welcome! Luckily Nordstrom has free returns.

  3. Just recently found this post and Love, Love Love it❣️

  4. I do love looking at your posts. Love wearing shorts in the summer but the cost of clothes today has me in a funk!

    1. It’s a challenge I know, so I try to share lots of price points.

  5. I just love your blog, Jennifer. I’m 5’9″ and sort of shy away from shorts but said the heck with that! I live in SC and it gets HOT here. Last year I bought the Chico’s Bridgette shorts and LOVE everything about them….the comfort, the length, the front pockets. I bought the red/orange pair and thought that that color might be waaaay to much but I love them. I went back to Chico’s last year for more colors but there were none. I thought that they discontinued that style but low and behold you brought them to us!! Thank you! Thank you! My cc is in hand. Have a great rest of your day and thank you for all of the amazing things that you bring to us.

    1. Yay! I’m glad you’ve found them again! They’re very flattering and comfy.

      1. Thank you!! I just love your blog.

    2. The Bridgette shorts sell out fast!!!

  6. Joyce Morey says:

    I’m so happy to have discovered you! As someone who is a bit older and no longer my slim, younger but still trying to be fashionable self, it’s fabulous to see someone who isn’t a skinny 20 year old, anorexic model and who is showcasing clothes I can picture myself wearing. I do wear shorts and I think I’m going to be ordering some Chico’s.

    1. I really like the Chicos shorts. They’re very forgiving because of the stretch.

  7. Keeping cool…surely dresses and skirts are the best option? Let the wind blow to cool the lady parts.

    Re shorts…My personal opinion is that knees are not the most attractive parts of our bodies—take a close look at them in the mirrow…. and as one grows older, even legs may lose their attractiveness. I go with ankle length pull-on cotton pants but then I am 87…and still having fun with style. However, you will not see my knees or elbows…the really wrinkly parts.

    Smiles are the best things to wear and they are always in season.

    Thanks for your posts. They keep me alert to looking my best no matter how old I am.

  8. Terrific post! Your tips and pics are extremely helpful. Especially with shorts right now. Thank you.

  9. Hi Jennifer….a couple of questions!

    How is the sizing on the AT sleeveless mock neck? Is it a slim cut? Go up a size? It looks great on you.
    And would you please, please explain/show how you tie a shirt at your waist? I can never get mine right. Love that look on you, btw.

    And Thanks for some good info.

    1. I sized up because of the knit. It’s a very nice top.
      I’ll try to get some photos or a video of how I do it

  10. I really appreciate knowing the inseam of the shorts you tried on. When looking at websites, the inseams are given but the models are often very tall and slim, so it’s hard to tell how long they would be on someone 5’2. Thank you!

  11. Your thorough review on different lengths of shorts is greatly appreciated. I also often wonder about tucking in a top. Thanks for the 1/3-2/3 rule. I look forward to reading your blog every morning. 👍

    1. Good morning, Judy!

  12. I never wore shorts because of a varicose vein problem. Had vein work done and now I will wear knee length shorts but no short shorts fit this gal.

    1. They’re a great option!

  13. Thank you for posting this! I love the Chico look with the layered tops. You are amazing! Good tips about 50/50 vs 1/3 & 2/3 split.

    1. I actually love the Chicos shorts too. They’re so comfy and versatile.

  14. Donna Groden says:

    I love this article. Thank you for all the styling tips for shorts.

  15. I really never wear shorts but I really like the longer Bermuda ones. I might give those a try. They all look great on you!

  16. Jeri Stodola says:

    Since I’ve had both knees replaced and still have scars from the surgery, I do NOT wear shorts. I’ve heard that capris aren’t in fashion, but they are what I wear in the summer.

    1. You may decide to accept the scars at some point and embrace shorts again. Glad your knees are fixed. It’s a miracle what they can do these days.

      1. Jeanne Claire says:

        This is a very helpful post, Jennifer. I am a shorts wearer but thought I would have to give them up because I have had both knees replaced since October of last year. What I hadn’t counted on was how readily the scars have faded. There must be new techniques in place because the October knee scar is almost invisible and the one from this April is rapidly fading. It’s totally amazing to me and certainly not like scars from other surgeries. So now I can continue to eye those cute Talbots gingham shorts with a thought 💭 towards actually wearing them! Thanks also for your tips on the right shoes for various lengths of shorts. That’s great information.

      2. Yay! I’m so glad this was helpful.

      3. Was just in Palm Springs and Rancho Mirage this weekend! All I saw were Capri’s! I will still wear them, it’s the length I like!!! Be brave!

    2. Sydney Haskell says:

      Jeri, I too had my knee done and have that terrible scar. I am 5’2” and wear the 12 regular size which brings the length just over my knee cap. I get the Sara by Liz Claiborne from JCP online. I now have 7 pairs in different colors and fabric choices. It gets so hot here that shorts are a must. Dresses just get in my way with bending over chores like scooping the cat boxes. I do have two pair of Sara capris but be aware that the denim fit tighter than the sateen fabric. I got mine in the 40% off sale in March but they have sales all of the time. I wear 12P in jeans but in denim I buy the 12 regular again in the Sara as it is so comfortable to wear. I weigh 140 pounds and am 78 so I agree with Mel about not showing the jiggly bits.

    3. I am apparently lucky. The scar from my knee replacement is pretty faint (surgery in March if this year) but does get more noticeable if I’m working the knee/leg hard. My family has encouraged me to keep wearing my shorts – that it’s something I notice more than other people do.

  17. I love the A-line look of the pleated shorts that have a longer inseam. They create a flattering silhouette & (as you pointed out) are more versatile than their straight-line cousins. The fact that these are unlined (cool) & a linen blend (low maintenance) is even better. I might be at Nordstrom this afternoon.

  18. I do love Chicos shorts because of the stretch and they come in petite sizing. Thank you for showing all the different styles and ideas.

  19. I look best in shorts that are a couple of inches above my knee, so most of these would not work for me unless I hemmed them. The Nic & Zoe top is pretty but the pattern doesn’t line up in the front and for that price, it most definitely should!

  20. Thank you for your opinions and insight. I was enjoying wearing skorts until I decided my legs and age did not look appropriate. I find wearing summer dresses more flattering and cooler.

    1. Many ladies feel the same way.

  21. I love the jCrew Bermuda short and 7” chino short. They have some give and are very flattering. I just wish they came in more colors thanks for the shorts ideas. I love that you tell us about them and show us what they look like.

    1. Sadly my J Crew closed so I’ll have to order some in.

  22. Thanks for the insight about tucking or not tucking a shirt!

    1. I hope the images illustrate why.

      1. Sydney Haskell says:

        Love the side by side images! It is so helpful to see your balance rule live. I prefer the comfort of leaving my tops untucked. The rule will work with my new shorts. Waiting for my new striped shirt from Nordstrom Rack! Will wear it out and open over a tank with my You look great in shorts Jennifer!

      2. Thanks, Sydney. I am warming up to them after trying so many on.

    2. I appreciate the Tips you provide with your styling ideas. They help me quite a bit. It’s nice to have you try these on. While my body is very different from yours, I can still tell what’s worth exploring for me. Thank you

      1. I’m glad this is helpful.

  23. Pat Patterson says:

    A very good sunny morning Jennifer, at least here in the northeast 😀, hope it is in your neighborhood. You look great in each pair of shorts, you are very lucky to have very nice legs. I on the other hand, do not own a pair because of very unattractive legs, it’s a personal choice.
    Have a great day.

    1. Happy Thursday, Pat! The sun is just coming up and I think it’ll be a glorious day here. Have a great one.

  24. I don’t like to wear shorts because they tend to ride up on me and that is not a good look on anyone. I wear skorts or dresses in summer. Can you share where to find the collarless chambray shirt you’re wearing in the last photo with the white shorts? I love it!

    1. It was from Chicos several years ago, sorry. I found different cuts do ride up. I think short rises make I worse.

  25. Thanks, Jennifer. I love the NYDJ shorts as the best length for me is right on or below the knee. I like my calves but my knees not so much! I find that “skimmers” are awesome shorts for my 5’7″ body and I have found great options at Chicos and Dillards. Ruby Road makes a great, affordable pull-on “skimmer” and Democracy (at Dillards, also some cheaper options on Amazon). The later have cuffs that roll up or down and they sit right above the hip bone and are in heaver fabric. Love your blog! Thank you.

    1. You’re so nice and tall. Those extra inches make a big difference in shorts.

  26. Thanks for the shorts article. I like St John’s Bay Bermuda shorts at JCPenney.

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