Midweek Popup- Pleated

My daughter and I were returning a few things at the mall last week and spotted this window display. I immediately thought of you and wondered what you would think of it. The background is one of my least favorite colors but it was the clothes that intrigued me.

It’s time for our would you wear it pop up. Each week my friend Pam and I share a store mannequin and ask if you would wear what it’s modeling. I love the conversations that happen in the comment section and the sharing of styling ideas.

Pleats don’t ever seem to go out of style and are more popular than ever this year. Since I had my tall, gorgeous daughter with me, I had her model the look for you.vanessa connolly modeling pleat trend for summer 2020

So tell me, ladies, would you wear this look?

How could you style it to work for your shape and lifestyle?

Please keep your comments personal so no one’s feelings get hurt.

Debbie (a reader) asked me to find her some lightweight tennis shoes that lace up, have a cushy insole, and would look cute with shorts or a skirt. Not workout sneakers. She loves the look of Keds but they simply aren’t that comfy, and I would agree. Here’s what I found-


These come in multiple colors and widths with a padded collar, Ortholite® comfort-cushioned arch, Removable Purefit® dual-density foam footbed, and Rubber outsole. They are very highly rated for comfort and style. Here is the same sneaker in leather, if you prefer.

Paul Green has amazing technology and makes very comfy sneakers. They are investment priced but these ones are marked down heavily. This Naturalizer sneaker comes in several colors and has molded, dual-density cushioning and a supportive heel cup.


Sofft makes very comfortable shoes so I expect these sneakers are no exception. Clarks are one of my go-to for comfort this summer so I was happy to find these white leather lace-up sneakers.

These sneakers have a lot of positive reviews online, are made from ethically sourced materials, and have free shipping in the USA.

Now let’s go over to Over 50 Feeling 40 and see what Pam’s mannequin is wearing today.

Thanks for sharing your styling ideas and remember to wear what makes you feel confident.

This post may contain affiliate links which won’t change your price but will share some commission.


  1. Lori
    July 9, 2020 / 11:12 am

    The pleats are a bit too much for me as I like clean, simple lines. Your daughter looks lovely in the blouse. With my bust size, the dress would not work for me either, but I like the color. It’s funny that you mention the background color…I love that color! My daughter absolutely loathes it. It is just so interesting how different colors affect everyone.

  2. cindy
    July 9, 2020 / 8:02 am

    I love pleats but don’t care for florals on me. Now if I looked like your gorgeous daughter I might wear them!

  3. - Vicki Mikola Dack
    July 8, 2020 / 10:44 pm

    To tell the Truth, have always worn deck tennis shoes for “teddies” in navy blue with the wide white soles. As for pleats in clothing; not to keen on them. Hard to iron, usually end up scorching the garment.

  4. Debbie
    July 8, 2020 / 8:28 pm

    Jennifer, I can’t believe how fast you did research on comfortable tennis shoes for me. You are simply wonderful!! I will be reading the reviews to make my decision and I will link from your blog, wanting you to definitely get credit for the sale. As for the outfit, your daughter looks lovely in the blouse. It is so feminine and pretty. I am always a little uncomfortable in a sheer fabric, but with her age and figure she looks stunning.

    • Jennifer
      July 8, 2020 / 9:33 pm

      Please let’s me know if any work out for you! xx

  5. Joanna
    July 8, 2020 / 6:04 pm

    I have Clark’s sneakers in three different colours. They are comfy and look cute with almost anything.
    The top looks darling on Vanessa but I’m personally not a fan of distressed jeans, although I do like cropped for warmer days.

  6. Denny
    July 8, 2020 / 4:10 pm

    Your daughter looks great in the blouse. Me and my 74 year old Apple body, not so much. Love your blog.

  7. Sandy
    July 8, 2020 / 3:39 pm

    Now this was indeed an interesting post. I looked at all those pleats and thought, “Who in the world would good in either of those?” Then, I scrolled down and saw your daughter and thought, “Well, SHE would!!” So this has taught me that just because it’s not what I’d wear doesn’t mean it can’t look great on someone else.

    • Jennifer
      July 8, 2020 / 9:34 pm

      That’s one of the reasons I love the would you wear it posts. There is always a woman with great ideas on how to style things.

  8. Nancy
    July 8, 2020 / 2:53 pm

    I like the look of the blouse but the color would not.look good on me. is try it if it came in a more vibrant cor. The cropped jeans don’t appeal to me .at all. I”d choose a straight-legged mean The.dress.is.pretty but to o young looking.for me.

  9. Dianne🇨🇦
    July 8, 2020 / 12:59 pm

    I just love the pleated blouse!
    I wonder how it would look with white pants.
    I don’t tuck anymore!
    No to the dress.

  10. Pamela Over 50 Feeling 40
    July 8, 2020 / 12:22 pm

    I would not wear either the dress or the blouse. They are not designed for a curvy figure like myself, nor are they in colors which look best on me. Of course, your daughter wears it very well!

  11. Francesca B.
    July 8, 2020 / 11:47 am

    I cannot wear either of these, the dress or the skirt, as I have big boobs for my petite frame and I think it might make my top half look even bigger! So lovely to see your daughter, she looks ace in that blouse hope she got it! Happy days to all.

    • Jennifer
      July 8, 2020 / 9:35 pm

      She did buy the blouse:)

  12. Eve
    July 8, 2020 / 11:42 am

    I wouldn’t wear the dress but I think it would look lovely on a young woman like your daughter. I do like the jeans and top and absolutely would wear it if you can’t see through it. I’m avoiding ordering online because of the super thin fabrics and the tighter than normal skeeves on tops.

  13. Elaine @ Following Augustine
    July 8, 2020 / 10:44 am

    Those are not looks that I would wear, but the blouse looks great on your daughter and it immediately made me think of a close friend who I know would absolutely love it!

  14. Becky
    July 8, 2020 / 10:43 am

    While the outfit looks wonderful on your lovely daughter, I don’t think it would look that good on my short older self, nor is it the classic style to which I am drawn.

  15. Rose
    July 8, 2020 / 9:08 am

    WOW! That outfit looks so much better on your daughter! If I were her age and height, I would definitely wear it.

  16. Karen Young
    July 8, 2020 / 8:36 am

    On the topic of what I’d like to see on your site, have you thought about a day or two on how to wear vintage styles?
    Also, how about occasionally posting a reader’s photo in a look from your DRD’s?

    • Jennifer
      July 8, 2020 / 9:41 pm

      Great ideas! Thanks!

  17. beth byrd
    July 8, 2020 / 8:29 am

    Your daughter is just so lovely!

    I am crazy about this blouse — the pleats, the color, the style. It’s so feminine and has a vintage/boho vibe that isn’t overdone. I like that it is paired with jeans! I could see this blouse worn several different ways — dressy pants or a skirt!

    The dress is pretty but would like be flattering on me.

    I could picture that dress on a young woman for an informal or casual wedding.

    • Jennifer
      July 8, 2020 / 6:31 pm

      Thank you Beth, she’s a great gal.

  18. Deanne
    July 8, 2020 / 8:14 am

    Your daughter really brings that outfit to life! Gorgeous. But not my style at my age. Hope you’re enjoying your visit!

  19. Anon
    July 8, 2020 / 8:10 am

    Your daughter can carry this off. However, pleated tops can make those of us who are not so slim and young look bulgy. Bulgy is not a good style word.

  20. Debbie
    July 8, 2020 / 8:07 am

    I think I could wear the pants. They look comfy and stylish. The blouse is a big no because it’s polyester and way too hot for the summer!

  21. kathryn cunningham
    July 8, 2020 / 7:53 am

    love pleats. Your daughter looks just like you

    • Jennifer
      July 8, 2020 / 9:42 pm

      I take that as a huge compliment. Thank you

  22. Julie Traxler
    July 8, 2020 / 7:31 am

    Gosh, this is complicated! Right off, I wouldn’t have looked at that dress for me as it is too skimpy. Too much skin showing at my age. The color is beautiful, tho, and the fabric is lovely.
    I love the sheer blouse and jean combo (as your tall gorgeous daughter proved). It is romantic. I couldn’t do the front tuck as is displayed on the mannequin, and I would wear a camisole. I might wear it tucked in completely. I like the jeans, but I would have to try them on to see if they worked. I have a larger bottom than top. The Liverpool jean works well for me.
    Thank you for your suggestions for white tennis. I love them for summer!

  23. Kathy
    July 8, 2020 / 7:30 am

    The dress is a definite NO! I would definitely wear the blouse and jeans outfit! Great look.

  24. Terri
    July 8, 2020 / 7:22 am

    I love the jeans and pleated top and wouldn’t hesitate to wear them. It’s amazing how much better they looked on your daughter than just hanging in the display. The pleated dress was just too bare in the chest and back for me to consider.

  25. Sandra Baron
    July 8, 2020 / 7:05 am

    Love both. Of course your daughter would look beautiful in anything, but I find pleats cool & easy to wear.

    • Jennifer
      July 8, 2020 / 7:26 am

      Thank you. I’m so blessed she’s here to help when all this is going on.

  26. RPSMc
    July 8, 2020 / 7:02 am

    Beautiful on a tall young women like your daughter!!
    I wouldn’t choose this for me.

  27. Linda
    July 8, 2020 / 6:46 am

    Not my style. It looked fine on your daughter, just not into pleats and ruffles.

  28. Janice
    July 8, 2020 / 5:57 am

    The outfit does look great on your daughter, but I have a short neck and do not wear any shirts with that neckline too high. The dress would accentuate my hips that do not need extra material. I love the sneaker recommendations, I am still looking for a pair.

  29. Eileen
    July 8, 2020 / 5:54 am

    Cloth lace ups, Superga , leather lace ups, Ecco, are my favs. Pleated top, yes, I would wear in a different color way, and in silk, I’m a pear with small bust. Jeans no, I would wear linen, maybe a skirt. Dress, beautiful, very “ fortuni “ ( spelling probably wrong) I would pair with cropped leather/ suede biker jacket. Daughter, beautiful.

  30. Karen Needler
    July 8, 2020 / 5:40 am

    Another comment about the blouse: I was a “Dress for Success” big 4 accounting firm consultant in the 80’s and wore suits every day as dictated. Fast forward, my self-selected uniform of choice as a high school teacher is skinny jeans, Ecco soft 7 sneakers or sandals, and a blouse like your daughter wears. The blouse balances out the casual elements. In cold weather, I swap in booties and a cashmere sweater, jewelry for interest.

    I discovered Tucker silk blouses a few years ago, and while they are outside of my price range (over $200!), they can be found on ebay, poshmark etc. The silks are gorgeous, and stunning on women of our age.

    Bottom line, a blouse like this can be lovely on others besides your strikingly beautiful daughter. As others have said, I was going to pass over it until I saw her wearing it! 🙂

    • Jennifer
      July 8, 2020 / 9:45 pm

      Thanks for the tip. I’ve never heard of Tucker

  31. Christine
    July 8, 2020 / 5:36 am

    I’ve the floral blouse and frayed hem wide leg jeans – definitely my style. Like the juxtaposition of blouse and denim. The dress is a lovely colour but I don’t like strapless bras so would prefer a wider strap, not spaghettis.

  32. Karen Needler
    July 8, 2020 / 5:31 am

    At first I thought you were going to ask what we thought of nightgowns and robes; that would be fun and useful! I love the idea of the top and jeans, but I’m not a fan of these jeans on me. Your daughter really shows how great the outfit can be!
    Now about comfortable sneakers for everything — my 21 year old daughter and I each have two pairs (one white, one a diff color) of Ecco soft 7’s. She wore hers out of the box on a walking vacation in Europe last summer, and I wear mine teaching (when I’m in SCHOOL, remember that?) and any chance I get. Every time we slip them on, we sigh loudly at their comfort. They’re sleek, cushy and supportive and work with dresses, shorts, jeans, cropped pants, you name it. Definitely one to check out. I’ve never worn the slip-on, but they seem to have the same structure.

  33. Donna
    July 8, 2020 / 5:29 am

    Looking at the mannequin I would have never given the outfit a second look. It looks lack luster, drab and just seems to hang.

    On your daughter it looks Light, lovely and definitely something I would wear!

    After seeing the Pleated blouse, On your daughter I noticed the soft colours and soft fabric and I love it. Combining such a delicate, Lady like piece with jeans is fun and definitely allows for lots of options featuring this blouse. I would definitely try on this combo. I would also pair this blouse with a soft cream or pale pink tailored skirt for a work or date night outfit.

    Apple doesn’t fall far from the tree. Both you and your daughter a beautiful women.

    • Jennifer
      July 8, 2020 / 9:47 pm

      You’re so sweet. Thank you Donna

  34. Linda GR
    July 8, 2020 / 5:24 am

    I really like the blouse and I’d wear it with bluejeans, slacks, or skirts. The dress is lovely, and I’d have worn it in my younger days when everything was firm.:-)

  35. Connie Konidaris
    July 8, 2020 / 5:12 am

    Love the pleated blouse.Your daughter is a doll.Love

  36. Diane
    July 8, 2020 / 5:10 am

    I love the feminine verses the more casual look of the jeans. I always love this juxtaposition.

  37. MRSBEN2
    July 8, 2020 / 5:09 am

    Though I do have a few pleated blouses; I’m afraid this one with its pleated cap sleeves and neckline is not to my preference. (It looks amazing on your daughter though.) Also shall add, long sleeved sheer blouses when left open, make for great overlays when worn with camisoles and/or tank tops. As for the dress, perhaps if I were fourty years younger as do like its styling details and colour.

  38. Paulette Levy
    July 8, 2020 / 5:08 am

    I agree. Seeing the blouse on your daughter makes me think, yes I could wear this too. While jeans like these might work, id try white jeans for summer. It’s pretty!
    The dress, with knife pleats, is not for me. I have never liked that pleating on skirts or dresses, and I’d never seek them out.

  39. Mary Lou
    July 8, 2020 / 5:04 am

    I would have worn these lovely things in my 30’s. The dress for me now is too revealing but I do love it. The blouse is beautiful. I hope your daughter bought it.

  40. Joyce Reardon
    July 8, 2020 / 4:49 am

    The blouse looks lovely on your daughter. I might consider it with a cami. The dress would do nothing for me.

  41. Jan
    July 8, 2020 / 4:42 am

    Let’s Just say, right up front, your daughter looks amazing!
    Now on to the featured display. Both the dress and blouse have a vintage look and the pleats on the dress would show no mercy on my imperfect shape. I could see the jean crops working if they were full length. For me, this display is directed at a younger shopper. I don’t see very many situations where “pleats” would be my friend! Lol

  42. sheryl beil
    July 8, 2020 / 4:30 am

    i love the blouse, but pleats are just too much work to care for in my opinion. the dress is a no for me, pleats across my hip line would be like wearing a danger wide load sign, even without the pleats, a center waist belt line isnt my friend.

  43. Linda V
    July 8, 2020 / 4:15 am

    well, the blouse looks great on your daughter because she is tall and thin. I however have a large bust and stay away from pleats. I would not wear either the dress or the blouse at all. Also, I do not like the colors.

  44. Leslie
    July 8, 2020 / 4:15 am

    I would definitely wear this gorgeous blouse with a white cami underneath. Throw on some cute flat sandals for a casual look or some summery heeled sandals more a bit dressier look.

  45. Susan
    July 8, 2020 / 4:12 am

    Your daughter looks gorgeous in that shirt, because the shirt is meant for her age group, not mine. Same goes for the dress. Which is why I wouldn’t wear either.

    • Patti Shannon
      July 8, 2020 / 4:24 am

      Your daughter is very pretty and is the age and build (y’all and thin) for it…even with all that she adds to the outfit, it doesn’t blow me away. I don’t care for pleats personally and as I’ve aged and gotten shorter neither look would work for me. I agree with Susan that neither is for my age group. Also, 2 lumpectomies have left me more than a bit asymmetrical, so the pleats could be a real conversation starter; just not one I want to have!

  46. Diane
    July 8, 2020 / 4:09 am

    Seeing the blouse on your daughter (I’m assuming) sold it for me…
    I do like the dress for a summer wedding or party…

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