Popup Would You Wear It

Popup Would You Wear It

It’s time for a mid-week would you wear it. Each week my friend Pam and I share a mannequin on Saturday, but with everything that’s going on, we decided a little bit of normalcy and escape would be fun so we’ve added one to ward off the mid-week slump.

If you’re new here, would you wear it is when we share a mannequin or store display and ask if you would wear what is being modeled. Please keep your comments personal and helpful.

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

Does this work for your lifestyle?

Are the colors something you wear?

How would you style it to make it work for you?

Now let’s go to Over 50 Feeling 40 and see what outfit Pam is sharing.


Thanks for reading 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. Linda R Gaertner
    June 3, 2020 / 7:16 pm

    I like the outfit to look at but I’m petite and large breasted so I wouldn’t be able to wear the top. I do like the looks of the pants but I’ve never liked how I look in fuller pants. They add inches to my frame which I’m always trying to minimise.

  2. Carolyn G.
    June 3, 2020 / 5:43 pm

    I love this top and would definitely wear it. I would wear it with white or light denim slim leg or ankle jeans. The cropped wider leg pants aren’t for me. I love the sandals too.

  3. Janey
    June 3, 2020 / 4:52 pm

    I like the top, but not on me as I need a bra with straps. The pants look like nurses pants to me, I prefer tighter, cropped, or flowing styles. I love the look of the shoes but I have had that style before and found the strap around the ankle to be irritating.

  4. Patti Shannon
    June 3, 2020 / 2:03 pm

    The top is pretty but as many have mentioned, off the shoulders, short shirts and anything that requires a special bra don’t work for me anymore….maybe in my 20s but not mid 60s. Pants are always a difficult fit and I’m not wild about wide legs. The ankle strap would be aggravating and my arthritic joints require more support – thank goodness there are many great options now. I generally wear silver or white gold jewelry to match my silver hair. But the younger me would have definitely worn it!

    • Jennifer
      June 3, 2020 / 8:05 pm

      We are fortunate to have so many choices 🙂

  5. Eve
    June 3, 2020 / 1:06 pm

    I love this look and spent my twenties wearing this look all summer. I can’t wear off the shoulder anymore, sadly.

  6. Elaine @ Following Augustine
    June 3, 2020 / 11:27 am

    I don’t wear off the shoulder tops and I need a red with more orange in it, so the top is out for me. I like the rest of the look, but I would have to try on the pants and the sandals. I have a boyish figure and often have to try on many pairs of pants to find one that fits right. If they fit at the waist, they’re often too baggy at the hips. I also have a very narrow foot, so sandals that can’t be adjusted are often too loose for me.

    • Eve
      June 3, 2020 / 12:51 pm

      Elaine, I have that problem with pants. In jeans, I buy Banana Reliblic by waist size and they fit my hips without bagging. You might want to try them. A jean is a jean.😊

      • Eve
        June 3, 2020 / 12:53 pm

        Forgot to say, I buy men’s jeans.

  7. Dawn
    June 3, 2020 / 11:24 am

    No to the top although I love it. I don’t like polyester for summer and don’t wear off the shoulder tops at my age. I’d wear everything else pictured. I really like wide leg pants when it’s hot.

  8. Susan
    June 3, 2020 / 11:08 am

    I would wear the bracelet and earrings. I don’t wear crop pants or tops that require a special bra. I don’t wear sandals that need to be strapped on.

  9. Kay
    June 3, 2020 / 11:01 am

    I love it all! However, I have never been a fan of the off-the-shoulder style, and I have always just worn them as peasant blouses.

  10. Dagmar
    June 3, 2020 / 10:34 am

    I love the white pants, but not the shoulder free top. The sandals are cute.

  11. Jan Stout
    June 3, 2020 / 9:27 am

    I do love the look but wouldn’t wear the top as The elastic in the arms drives me nuts.I prefer a cold shoulder look..
    The wide leg crops are cute for summer. I am 5’4. @ 155# and they look good with a small heel as shown.

  12. Lily
    June 3, 2020 / 9:19 am

    I don’t buy anything that requires a special fit bra so the top is a no. I would not feel comfortable in full white pants.

  13. Linda
    June 3, 2020 / 9:11 am

    I find top and bottom pleasing. I think the top hs lovely in its design and color! White pants are always welcome! I think the Sandals might even work with my left foot for a few hours!

  14. Nancy Walden
    June 3, 2020 / 9:08 am

    I like the color, the print, and the flowy lines of the top but I don’t feel comfortable in off the shoulder tops. I’d have to try the pants on. I am not a fan of wide-leg pants but the high rise is appealing. I usually wear slim pants or a pencil-style skirt with a flowy top. I like the color of the sandals but I don’t wear ankle straps. I feel the horizontal line makes my legs look shorter. I like the bracelet and earrings!

    • Jennifer
      June 3, 2020 / 8:07 pm

      Thanks for explaining Nancy

  15. Pamela Over 50 Feeling 40
    June 3, 2020 / 8:51 am

    Sadly, there is nothing here that I would wear. My dermatologist says I have lots of wisdom…but the wisdom spots are tiny age age spots pretty much all over…so an off the shoulder top would not be flattering. For similar reasons, the only thing I could wear in this montage would be the bracelet. I use to love ankle strap shoes, but now they just both me. So glad there are fun options on the market when you have special issues like I do!!

  16. Penny
    June 3, 2020 / 8:49 am

    Now that I’m sixty, there are some things I have to think about wearing. The only items I would be totally comfortable wearing are the sandals and the bracelet. The off shoulder top is too short and not something I’m comfortable wearing anymore, the pants are the wrong shape for me, the earrings seem a bit dowdy. This outfit may look cute on someone else, but feel it won’t work for me due to age and the cut of the top and pants.

  17. Dianne🇨🇦
    June 3, 2020 / 8:07 am

    Really cute outfit, just can’t wear off the shoulder @ 74
    Love White pants !
    Lovely accessories.
    I really enjoy your blog,thanks.

    • Jennifer
      June 3, 2020 / 8:07 pm

      I’m glad you like them Dianne

  18. Holly
    June 3, 2020 / 7:50 am

    Love the entire outfit!

  19. Debbie
    June 3, 2020 / 7:46 am

    Red is not a color I can wear by my face and I don’t care for the off the shoulder look. Everything else looks great for a summer outfit. The wider pants would be comfortable and help balance my shape. I remember when I was a young mom thinking I’d never be able to wear white pants again with children’s sticky little fingers.

  20. Linda
    June 3, 2020 / 7:38 am

    Yes I’d wear this and I’m 73, but have been told I don’t look anyway that age.

  21. Terri
    June 3, 2020 / 7:05 am

    What a pretty summer outfit! My first thought is that I’d have looked really good in it 20 years ago at 5’ 8” and 130 pounds, but I’m not sure about now. I find myself thinking those kinds of thoughts more and more often these days, even though I know it’s not the right attitude. Getting older isn’t easy.

    • Jennifer
      June 3, 2020 / 7:42 am

      You’re expressing a struggle many of us deal with Terri.

  22. jmp
    June 3, 2020 / 6:30 am

    Love the color of the red top, but I can’t do the off-the-shoulder look. The white pants are stunning. Those would be a summer “go to” for a more dressed up look. I would also change the jewelry to silver.

  23. Donna
    June 3, 2020 / 6:18 am

    At first glance I love all the pieces but I would not wear them together. Flow-y top and wide leg pants would only serve to overwhelm my frame and make me look shorter and wider.

    I love the colour of the top. I would pair it with white skinny jeans or shorts or even a pencil skirt. I’m not a fan of the strings around the neck but if the top edge as it seems to pull the Centre of the top up and the shoulders drop down. No one needs droopy shoulders. I would have to see if that could be adjusted or removed entirely for it to truly work for me. But I love the colour.

    I love the cut of the pants , tapered at the waist and wider on the legs. I would pair them with a fitted T-shirt or a short fitted cardigan buttoned up For a casual look I would thrown on a Jean jacket for cooler evenings. You could also dress these up with strappy sandals and a silky camisole for evenings. Personally I do not like the lace detail but as it is the same colour as the pant it might not bother me as much in person.

    You can never go wrong with pearl earrings and the touch of gold just adds to that.

    The gold cuff is a classic.

    While I love the idea of the sandal, the colour and the heel height, I have yet to find a ankle strap to fits around my ankle. I also find the ankle strap cuts and shortens the line of my leg. Which is never a good thing.

    • Diane B
      June 3, 2020 / 6:34 am

      Wow! You and I must have the same built. I wanted to write “ditto.”

    • Jennifer
      June 3, 2020 / 8:12 pm

      Thanks Donna. That’s a wonderful explanation and so helpful.

  24. Linda
    June 3, 2020 / 6:13 am

    No off-the-shoulder for this large-busted girl. I just can’t get into the wide legged pants, either full-length or cropped (especially). White pants are tricky, and I usually stick to white denim as it’s opaque enough. I prefer silver jewelry now that I’m gray.

  25. Mary
    June 3, 2020 / 6:07 am

    Off the shoulder halter — nope — I probably wore that in the 90’s.
    98% polyester for that price? No
    The pants are too wide for me. I like the jewelery.

  26. MRSBEN2
    June 3, 2020 / 6:05 am

    Cute pieces but not for myself as feel off-the-shoulder blouses are for those well below my age group as to the pants do not care for HW (high water) length in such a cut. As for the jewelry love it but would prefer it in a silver finish. Last but not least re the ankle strap shoes; though would much prefer them in a leather a yes to them since I have always had difficulty keeping sling backs on my feet plus them being flats, presumably would be a comfort shoe.
    P.S.: We here in Canada usually wear suede in the Fall and Winter seasons and not so much in summer.

    • Jennifer
      June 3, 2020 / 8:13 pm

      You know it’s funny but I used to save my suede for fall and winter

    • Jennifer
      June 3, 2020 / 8:14 pm

      You know it’s funny but I used to save my suede for fall and winter too but the messy weather always destroyed the suede. Now I prefer mine in the spring and summer.

  27. Connie Haines
    June 3, 2020 / 6:00 am

    Red isn’t a good color near my face, so I’d pass on this particular blouse and look for it in a blue, yellow, or white. Lovely design, and I would absolutely wear off the shoulder in summer or on vacation. The cut of the pants is not flattering for me, so I’d go with a trimmer line. The sandals, while cute, wouldn’t be my first choice. I have a nice pair of neutral toned open toe sandals with 2″ heel that would work nicely instead, and I agree with several other ladies that I’d choose a hoop earring – silver, or gold.

  28. Eileen
    June 3, 2020 / 5:58 am

    As a pear, the silhouette isn’t ideal, as I would need a light top that’s more fitted, and darker bottoms. The top is polyester so, I would not wear it, too hot for my climate. The pants are cotton which I love, and high waisted, which I like, but I don’t care for cropped styles, I question the lace placement at the waist, as it adds extra fabric . I would wear them as knee length shorts, minus the lace.

  29. Joy
    June 3, 2020 / 5:58 am

    I live the entire look except I couldn’t wear the sandals. My legs are too short and anything with an ankle strap looks awful on me. I wouldn’t wear the jewelry just because I only wear my watch and wedding band. The top and pants I love.

  30. Vickie
    June 3, 2020 / 5:53 am

    I have a carrot body type-so- The top would make me appear even more top heavy than I already am. The white pants would work better for me to be a straight leg, flare, or bootcut And longer for my petite frame!
    Sandals and jewelry would work for me – I would add a long pendant necklace!

  31. suzanstew
    June 3, 2020 / 5:43 am

    Most of these outfits in the “would you wear it” series scream “NO” to me. Not this one. I love all of this, colorwise. Some elements, like the ankle straps, I could see myself finally breaking down and wearing. I do have to say, I’d probably be more comfortable in a top that had shoulders and slimmer pants, but this might get me out of my comfort zone. Wish there were Ann Taylors or open stores around me and I might run in and try.

    • Jennifer
      June 3, 2020 / 8:16 pm

      We do choose our outfits at random so sometimes no one likes them:)

  32. Deborah
    June 3, 2020 / 5:29 am

    I love the look but might change a few of the elements. The white slacks would probably become white jeans. The top I like but I don’t wear red and I would see if it could be worn on the shoulder and snip those strings off . The strings are not good on my aging neck. I would do a similar neutral shoe but without an ankle strap,too much swelling in an old formerly broken ankle. And while I mosy often wear silver i really liked the jewlery especially the earings!

  33. Lidia Mascolino
    June 3, 2020 / 5:18 am

    I love the overall look but the particular top and pants would be problematic for me. I’m not a fan of off the shoulder, even though this has the neck tie which gives it some support. I prefer shoulder-skimming and this color does not work for me at all. So that would be a definite no. At first glance, I loved the pants but at closer look, the novelty trim would be deal breaker – makes them look too “stylized”. As for the rest of the pieces – love them all.

  34. Corrie
    June 3, 2020 / 5:17 am

    I would like this better if the top were not so orangey-red (I’m a “summer”), and if it were not off-the-shoulder. The pants are nice, if I dared wear white – I’m a dirt magnet – but jeans would suit my lifestyle a little better. The jewelry would be great if it were silver, but the shoes are a no-go, since straps that encircle the ankle make legs look like stumps. So I guess you could say I wouldn’t wear this exact outfit, but I can see it on someone else 🙂

  35. D
    June 3, 2020 / 5:16 am

    No white pants for me wore white often as a nurse white pants always say work pants sorry love the red top but not the style

    • Jennifer
      June 3, 2020 / 7:45 am

      The memories we have of clothes are so influential.

  36. Diane
    June 3, 2020 / 5:01 am

    I like that the look is a little sexy and a lot polished, I would wear this look but would also pair the top with jeans and hoop earrings for a more casual look.

  37. - Vicki Mikola Dack
    June 3, 2020 / 5:00 am

    Don’t wear white trousers of any style…jeans, capri, dress…perfer dark shades…as for the top, no thanks….am pear shaped (narrow at the top/wider in the bottom=hips/thighs) and don’t like to show my shoulders nor chest areas. Prefer tailored and classic styles. Usually wear 3/4 sleeve and v-necks.

  38. Jan
    June 3, 2020 / 4:54 am

    The solid base color and small print on the top is very forgiving for my not so perfect shape. I am not a fan of the off the shoulder look and would prefer a boat neck or square neck style. The pants are gorgeous. When you put both pieces together, it’s a lot of fabric on my shorter frame. I would pair the pants with a more fitted jacket. The accessories seem to go well with the pants. I would anchor the top with a stronger color in my accessories. I’m in agreement with another comment that the top would pair better with denim for my lifestyle.
    Thanks for post Jennifer!

  39. Linda GR
    June 3, 2020 / 4:43 am

    I like the color and pattern of the top, but I don’t wear off the shoulder style. I’d wear the slacks, and I love the jewelry. I don’t wear ankle strap shoes, so I’d style these with flats, or a wedge heel.

  40. Cheryl Mueller
    June 3, 2020 / 4:42 am

    Love the look…but prefer dark pants and would probably cut off the neck strap and wear the top up on my shoulders.
    Cute accessories!!

  41. Carol Leeson
    June 3, 2020 / 4:38 am

    I love the color, but would not personally wear the off the shoulder blouse. As a plus size woman, that would make me feel too self-conscious. But I love the colors and the jewelry!

  42. sheryl beil
    June 3, 2020 / 4:33 am

    i do love the top, but ive never found a strapless bra that didnt have me pulling and tugging constantly….i would swap jeans for the slacks, and the jewelry a little more boho than classic…the shoes are a no for me, ankle straps annoy me….but some upscale flat sandals or wedges would work for me.

  43. Lori Stewart
    June 3, 2020 / 4:13 am

    I love the entire outfit but would have to get a strapless bra to wear the top, I am too busty to go bra free. I love the color and print on the blouse and the classic style of the slacks. The jacketed pearl earrings are cute, but maybe a drop or hoop earring might work better with the feel of the outfit. The bracelet is lovely and the sandals compliment the outfit. This outfit says to me a nice dinner on the shore.

  44. Glenda
    June 3, 2020 / 4:11 am

    Yes!!👏🏻👏🏻 Love this summery dressy look. 😊

  45. Liz
    June 3, 2020 / 4:09 am

    So summery! The top, definitely, but with white or blue denim and blue/white bracelets and dangly pearl earrings.

  46. Martha
    June 3, 2020 / 3:53 am

    Love the top! I’d definitely wear it. The jewelry and sandals are a yes, please. Just my style. The pants look great with the top…white pants are so summery! But I think these are a tad too wide in the leg for me. Especially towards the ankle. They’re cute…I just never look good in this style. I guess I’m too short and curvy!

  47. Paulette Levy
    June 3, 2020 / 3:20 am

    Yes! I absolutely love the off shoulder blouse and own a couple of these tops already! The jewelry is pretty and though I tend to silver jewelry, I’d wear these pieces…..onto the trousers here. I like that they are white but I prefer a more palazzo flowy pant leg. These are wide but don’t have that line I prefer. I’d need to try these on before making a decision. So other than the particular pant this grouping is a YES!

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