Would You Wear It: Casual Classic

Would You Wear It: Casual Classic

Happy Saturday ladies and welcome to your weekend. I took several days off from the blog and social media for family time. It felt very strange not to be posting, but it felt so good to focus on loved ones. I have hit a few after Christmas sales, but frankly, I am almost shopped out.

Each week my friend Pam and I share a store mannequin and ask if you would wear what it’s wearing, We do this to better understand your style goals and foster conversation in the comments.

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

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

What accessories would you add?

In case you didn’t get what you wanted for the holidays, it’s all on sale now! Here’s an update-

Nordstrom – the Half-yearly sale is in full swing with up to 50% off. My faux fur I am loving to bits is on sale 50% off so if you like it, now’s a great time to get it. I ordered a few cashmere sweaters for my husband at this sale, because the prices are amazing!


Pottery Barn – up to 70% off with the code SAVEMORE


J. Crew – 50% off sale with the code BIGSALE


Ann Taylor –  40% off new merchandise and an extra 60% off sale. My daughter and I always this sale because we love their things.


Talbots – their famous Red Hanger sale is on which is their biggest of the season. There are some fresh new colors for spring which are a breath of fresh air.


Loft – 50% off full-priced styles.

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

Thanks for reading and be sure 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. Lynn
    January 1, 2020 / 8:28 pm

    Well. I laughed a lot when I read the comments that said the color of the mannequin is ‘inclusive.’ I had to scroll up to the picture to check. It is grey, and yes, I am old and grey. Rolling on the floor laughing.

  2. Lee Wilkinson
    December 29, 2019 / 5:54 pm

    Interesting outfit with the more formal top and casual jeans and very wearable. I like the top, although collars that go into the neck like that no longer suit my ageing neck. For the same reason, I’d wear a pendant, coming down into the v, rather than that neck-hugging length. I do like the light blue denim with the white top. Now I am grey haired, with blue eyes, a lower contrast looks better on me. Pre-grey hair I’d have put dark denim with this. The clutch bag looks odd – a casual look like this needs something more practical.

  3. Lisa
    December 29, 2019 / 10:46 am

    Love the entire outfit, especially the blouse. The jeans are a little too baggy but would definitely wear them if they were tighter. I like the purse but wouldn’t buy it because it’s too small and looks awkward to carry around – I need to be able to hang my purse over my shoulder to be hands-free.
    The necklace is pretty. You could change the look of this outfit with different accessories and shoes/boots.

  4. Theresa
    December 29, 2019 / 5:39 am

    Love the look, bag is not my style, I would probably wear a small shoulder. The top is exquisite, it can be worn So many different ways. Just ordered both.

  5. Susie D.
    December 29, 2019 / 2:21 am

    I really liked the blouse. It had such nice details. The buttons, and the sleeves that were set in and puffed just the tiniest bit at the shoulders. It was very feminine but not overly fussy.

    That particular style and color of jeans would not be something I would wear with such a pretty blouse, but that’s just me, I suppose many people would like the contrast between those jeans and that blouse.

  6. Susan
    December 28, 2019 / 7:20 pm

    Great outfit. French tuck the shirt and add a jacket for me!
    Buying this time of year during womens retail annual sales events at 50 to 60% off is such a win for wardrobes. Finding that amazing piece at a great is such win.
    Hope you had a fantastic holiday ❤

  7. annie vanderven
    December 28, 2019 / 2:55 pm

    Love the shirt, but I hate jeans, the handbag is a nice modern touch

  8. Deb
    December 28, 2019 / 2:17 pm

    Would wear if I had a waistline! With a small black velvet belt and silver/black jewelry. A shoulder bag too!

  9. Cathy Wright
    December 28, 2019 / 1:39 pm

    Yes, I would wear the outfit but not the purse? While I love the color of the purse, not a fan of wristlets. The blouse is a classic which is my style and I like the lighter wash of the jeans, it is refreshing. Would wear neutral booties in keeping with the lighter pallets.
    Happy New Year. Glad you took time for you and family.

  10. Cathy Cunningham
    December 28, 2019 / 1:33 pm

    Love this outfit! Yes, I would wear it.

  11. Becky
    December 28, 2019 / 1:14 pm

    I love the blouse. It could be dressed up with a suit or even a velvet pant. If I were wearing it with jeans, I would choose a dark rinse, as I am not a fan of faded jeans. I don’t care for the bag, I would want it smaller for a dressy occasion or larger for everyday use. The necklace is pretty & lets the blouse shine. I would add flats or boots for footwear.

  12. Cheri
    December 28, 2019 / 12:41 pm

    A simple but elegant outfit that could be worn most anywhere. I would possibly add a pretty silk scarf or some simple jewelry but even without those the outfit would be lovely.

  13. Susan
    December 28, 2019 / 12:05 pm

    Say yes to the blouse,better with darker jeans, can the clutch! A hobo would look better in a neutral shade!

  14. Mary Ann
    December 28, 2019 / 11:01 am

    Pretty blouse. Eh jeans. Kind of sloppy looking. Purse, no. And definitely untucked in front. Not everyone has a flat belly… ;-(

  15. beth byrd
    December 28, 2019 / 10:22 am

    This is such a great outfit! I love everything about it. It is classic and stylish. I could see myself wearing this often!

    I’m not keen on the clutch, but it adds a pop of color and styling that is unexpected. It might grow on me!

  16. Barb
    December 28, 2019 / 10:20 am

    Enjoy the outfit. I would wear the blouse but would wear darker and more fitted jeans. I would also add a blazer or motor jacket for completeness. As I am very petite I would tuck in the blouse to hopefully extend my legs somewhat. Especially enjoy the V neck on the blouse, as this is my preferred neckline. So hard right now to find V necks in anything!

    • Jennifer
      December 28, 2019 / 12:14 pm

      Tucking the top in would elongate your legs. Great idea.

  17. Dianne
    December 28, 2019 / 9:53 am

    I love the blouse!
    White & crisp but still comfy.
    No to the purse.

  18. Elaine @ Following Augustine
    December 28, 2019 / 9:46 am

    Though I tend to wear a darker wash jean, I love this outfit and would wear it as shown. Stark white isn’t the best look for me, but I checked the website and discovered that the blouse is actually ecru which would be perfect.

  19. Eileen
    December 28, 2019 / 9:29 am

    The look is a nice classic look, easy to wear, I prefer natural fabrics, so I wouldn’t wear the top. I love the color blue, so I am eyeing the blue options coming this spring.

    • Jennifer
      December 28, 2019 / 12:15 pm

      There is a lot of blue around! It’s on my radar too.

  20. Eve
    December 28, 2019 / 9:13 am

    I prefer crossover bags and darker jeans. The blouse is pretty but I really don’t like sheer blouses. The necklace does nothing for this outfit. However I do love white, cream or ivory tops with jeans. If I paired it with a red corduroy jacket and brown boots it would work. That purse is just too big to be a wrist bag IMHO

  21. Linda
    December 28, 2019 / 9:10 am


  22. Lynda
    December 28, 2019 / 8:43 am

    I’d wear it in a heartbeat! I think the softness of the blouse and slightly looser fit of the pant would work wonders at balancing my large chest. I’d probably pick a suede loafer and keep it casual.

  23. Beth
    December 28, 2019 / 8:33 am

    I love everything about this outfit! It can be dressed up or down, depending upon the shoes you choose. Also would look great with a cardigan or blazer. I especially like the purse. Handbags are my weakness. This one is beautiful! Happy New Year!!!!

  24. Cheryl
    December 28, 2019 / 8:28 am

    I like this look. While I might not do it exactly as shown, I would go for this look. The jeans do look a bit more casual but those can be changed out and keep look the same.

  25. Julie Anne
    December 28, 2019 / 8:27 am

    Yes, I’d wear it.

    The jeans look comfortable and I prefer a boyfriend cut. When I checked the link, these were quite form fitting.

    I’m another who no longer wants a collar on my shirts. Being short and having a short neck, I find a collar too overwhelming.

    No to the purse.

  26. Anne
    December 28, 2019 / 8:26 am

    I find the blouse lovely and would definitely wear it. At first glance I would have said no to the jeans, too light in color, however now that I have been wearing lighter jeans that fit loosely my opinion has changed. I thought the baggy sort of mom type jean would only look best on a skinny younger girl but I was wrong. The style of jeans pictured as well as baggy or loose fitting jeans look great on a much older out of shape woman like myself. It took a little getting used to and playing with different style tops but I find the jeans so comfortable:)

    • Jennifer
      December 28, 2019 / 12:13 pm

      This style is very comfy and styled right, very cute. I love mine.

  27. Peggy
    December 28, 2019 / 8:24 am

    I would wear it in a heartbeat.

  28. Dawn
    December 28, 2019 / 7:54 am

    I love the look! It’s classy and laid back, and looks very current. The blouse would work with everything in my closet. I might wear a slightly longer simple necklace. The purse adds a pop of color, and I’d add black flats. For the holidays a black or navy velvet blazer would be fabulous!

  29. Corrie
    December 28, 2019 / 7:52 am

    I would wear the blouse, depending on how the hem is finished and how long it is. I don’t “tuck” – that part of my body needs camouflage! I would wear dark wash jeans with this, preferably boot-cut, and a cross-body bag in either black or brown.

  30. Bernice Hearn
    December 28, 2019 / 7:52 am

    I love this outfit, very casual, and the blouse would look great with a pair of pants or a slim skirt and heel. That purse is not my style, would switch it out for a handbag.

  31. Lydia Barnard
    December 28, 2019 / 7:50 am

    In three words…Wrap it up!

  32. Paulette levy
    December 28, 2019 / 7:49 am

    This is ME! The purse works too.

    • Jennifer
      December 28, 2019 / 12:11 pm

      Don’t you love when that happens? I do.

  33. Sharon Mulliken
    December 28, 2019 / 7:48 am

    I love everything about this outfit! Due to my round middle, however, I would add a blazer or cardigan for camouflage and warmth here in the midwest lol. And I agree with everyone on choosing a sleek over the body purse…I have a gold one that would look great with those shoes!

  34. Donna
    December 28, 2019 / 7:34 am

    I like this outfit! Classic. I would change out the bag. Not enough room in a clutch to carry all my stuff lol

  35. Lily
    December 28, 2019 / 7:27 am

    This look is a home run. I would notice a woman wearing this and notice her for the right reasons. The look is classic taken up a notch. This is how real women want to look, Modern but not weirdly out there.

  36. - Vicki
    December 28, 2019 / 7:16 am

    Like the over all appearance. Handbag a tad too large for me to handle. Agree, could wear ballet flats or heeled leather booties. And add a cardigan styled or blazer jacket with a darker shade of jeans.

  37. Rose
    December 28, 2019 / 7:03 am

    I would wear this outfit but would like the jeans to fit tighter. The bag is cute but too big for me. So nice you had your family with you at Christmas. We had 3 of our kids and 5 grandkids, it was busy!

  38. Darlene
    December 28, 2019 / 6:57 am

    Love the entire outfit! I don’t think crossbody bags look. That great on women with big breasts. So I like clutch

    • Jennifer
      December 28, 2019 / 12:09 pm

      I agree crossbody bags can be awkward to get right if you’re busty.

  39. Lea
    December 28, 2019 / 6:37 am

    This is a great outfit! I might add a longer necklace and a different bag, I have one in that colour. An easy look to dress up or down and fun to accessorize.
    Always nice to relax with family during this time of year.

  40. Ann M
    December 28, 2019 / 6:35 am

    I’d wear the blouse in a heartbeat… it’s classy and I love the v neckline. I’d pair it with nice dress pants. While I like to carry a wristlet as they’re so easy and don’t get in the way at a restaurant (not a fan of putting my bag on the floor), this one is a bit large as a wristlet. The jeans… well, I’ll just say I have a pair like that for gardening and scrubbing the shower tiles, ha.

  41. Becky
    December 28, 2019 / 6:29 am

    I would definitely wear the jeans and top – I don’t care for the color of the handbag, so I would pass on that. For shoes, I’d probably wear boots

  42. Jen
    December 28, 2019 / 6:24 am

    I’ve had to switch everything in my wardrobe as I’ve developed a metal allergy. So frustrating as I lived in jeans. Life never ceases to add surprises!

    • Jennifer
      December 28, 2019 / 12:08 pm

      Oh no! That’s really a drag.

  43. Mary
    December 28, 2019 / 6:16 am

    Love this outfit! It fits my more casual lifestyle but is not boring. Like the pop of color in the purse, although it is not a very practical shape–too thin to carry everything but too large to just throw in a phone and cards. But it might be worth a try. or accessories, I would stick to the more dainty jewelry shown–afraid my bulky French Kande necklaces would hit those buttons. Flats or boots would work with these I think.

    • Jennifer
      December 28, 2019 / 12:07 pm

      I love the boots idea.

  44. RoseAG
    December 28, 2019 / 6:10 am

    I would be thrilled if I could find a pair of jeans that fit like this. I’d add a belt and probably a jacket or sweater.
    I also like that the manequin is not stark white. I was shopping in a mall near my home, which is a very diverse area and noticed that all the window displays had menequins that were this color. I think it’s more inclusive.

    • beth byrd
      December 28, 2019 / 10:20 am

      Oh I must agree with you about the mannequin. It is much more inclusive.

  45. MRSBEN2
    December 28, 2019 / 6:02 am

    Beginning with the blouse; do like its styling with its mandarin collar and v-neck as would have the option of adding a larger scarf (square/tied with a ‘v’ drape) to add some pattern and color to the outfit and possibly eliminating the need for any type of undergarment (slip/camisole) for opaqueness. (Its difficult to determine just how sheer the fabric is.) As for the jeans, do like their styling however would purchase them in tall for a longer length then adjust to my needs. i.e.: Type of footwear. With respect to their color prefer a darker wash for our Winter Season but certainly would wear them otherwise. Regarding the necklace; would add a 3-4″ extension to what is shown as prefer a longer drop to distract from my neck/jaw line (thanks to aging and its cheaper than cosmetic surgery… lol!). Last but not least; even though I like handbags that offer the option of a wrist strap, I feel the one shown looks out of proportion due to its long length with lack of depth so I would not purchase it but do like its color. -Brenda-
    Footnote: As seldom use handle totes anymore; for hands free convenience and to get two purses in one, I often create a wrist strap by using the excess strap from a cross-body bag then attach a ‘swivel trigger toggle clip’ to it.

    • MRSBEN2
      December 28, 2019 / 2:43 pm

      Well I’m not too bright, as just read the description of the blouse and a customer’s comment (lesson learned) and it appears its body appears to be lined which is a bonus however IMHO the shoulder line looks as though it is space-tucked (which creates ‘soft even’ pleats) and not pin-tucked as described, which normally constitutes visible stitches depending upon the type.

  46. Conda Bell
    December 28, 2019 / 6:01 am

    I would wear this look. Since it is a casual outfit, I would choose a different style of bag that would be easier to carry, but I love the color. The top would be great for work.

  47. Brenda
    December 28, 2019 / 5:50 am

    looks very cool and chic. You could dress up the blouse with “fancy pants”. ie linen, wool or velvet.

    I like the casual but smart look on the model. I think most body types could wear this outfit.

    Glad you had a good Christmas Jennifer

  48. Deborah Broughton
    December 28, 2019 / 5:44 am

    Love the concept of this outfit, the dressy blouse with jeans and the necklace. I would wear it but with different jeans ,dark wash or even the light wash but better fitting. Sorry but I might wear those jeans on Saturday in the garden!
    Would love to add a scarf, jacket or vest ..lots of options!

    • Tina Butler
      December 28, 2019 / 6:43 am

      I agree with Deborah. The blouse is a yes, but the jeans are a big no. The clutch needs to be upgraded. I think handbags and jewelry can really elevate even a very casual outfit.

  49. Donna Nance
    December 28, 2019 / 5:43 am

    This outfit is a whole lot less offensive than some! lol I do love the blouse and all the pretty detailing. Would probably wear a dark wash denim.

  50. sheryl
    December 28, 2019 / 5:33 am

    Love the blouse, i would switch the jeans to a dark wash, and either boot cut or skinny.
    the bag doesnt work for me, i need a shoulder or cross body.

  51. Amy
    December 28, 2019 / 5:33 am

    I would wear this in a heartbeat, it’s a classic and lovely look. I love collars and do wear them often, especially in the winter, but I also wear this neckline. With an even darker denim I would wear it to work. I also would use choose a larger necklace. I like the “tiny” necklace trend, but still prefer something with a bit more of a statement. I wouldn’t carry that bag. It’s an odd size, too big for a wristlet. Happy Saturday.

    • Jennifer
      December 28, 2019 / 12:07 pm

      Happy Saturday Amy

  52. Debbie
    December 28, 2019 / 5:30 am

    Yes-a versatile look for my retirement and volunteering lifestyle. As a classic dresser, a plainer or collared shirt in ivory would be more my preference.
    I prefer dark , skinnier jeans when not at the horse barns and would add a boyfriend cardigan to match the purse and statement necklace, though probably should be more into scarves…. with either boots, slides or ballet flats, it’s a go anywhere look.
    Thanks for the inspiration!

    • Jennifer
      December 28, 2019 / 12:06 pm

      Thanks for sharing your styling ideas Debbie

  53. Lois Williams
    December 28, 2019 / 5:06 am

    Yes I could wear this outfit just as it is. However, even better, would be dark navy, better fitting jeans with an added blazer – maybe a Talbot plaid.

    • Jennifer
      December 28, 2019 / 12:05 pm

      I love that idea. Navy blazer!

  54. Linda Phelps
    December 28, 2019 / 5:04 am

    I love this look! I would need to see how the jeans actually fit before I would purchase them (might be too short). I would not carry the purse, however.

  55. Norma
    December 28, 2019 / 5:01 am

    I do like this outfit,I don’t own light wash denim but willing to try. I too prefer crossbody purse . I’d add some jewelry and cute shoes.

    • Jennifer
      December 28, 2019 / 12:04 pm

      Cross body bags are a favorite with many of us 🙂

  56. MP
    December 28, 2019 / 4:58 am

    This is my look! Classic pairing of a white blouse and straight jeans. SIgn me up! Add black flats or black booties and off I go. I would not buy the purse. I don’t like the clutch style and it’s too big for a wristlet.

  57. Linda Gaertner
    December 28, 2019 / 4:47 am

    I like the look of the blouse and the jeans and would wear them. I not excited with the purse and would not buy it.

  58. Sandy
    December 28, 2019 / 4:44 am

    I really like this “no collar” blouse. I’d wear it. I’m not sure why, but I’m with Linda J. above. I don’t wear collars anymore. Wonder why? Are they still in style? I also like this blouse because it doesn’t have buttons down the front. Being rather busty, I can’t wear a blouse that buttons since they tend to gape open. This blouse isn’t fitted and I like that, too. I might be able to wear it tucked in since it’s bigger, but I usually wear tops out over my pants. The blouse looks dressy and the cut/color of the jeans looks casual. I don’t like that look together. I like the top and bottom to be the same type – either dressy or casual.

    • Susan
      December 28, 2019 / 6:23 am

      I like the whole outfit.I like making the dressy shirt seem more casual with jeans.I also don’t like collars,something about the angle on my face.The looser jeans seem like they need to be worn with the top tucked or with a shorter top.I think it’s done right

  59. Sondra
    December 28, 2019 / 4:23 am

    I would wear this outfit…definitely. Only exception is the handbag. I prefer a crossbody but do have a few larger bags in my collection.

    • Gwen
      December 28, 2019 / 5:47 am

      I really like the look. Blouse could be casual or work appropriate. Jeans look comfortable. Not sure about the purse. May or may not be practice depending on what I was doing at the time.

  60. Linda GR
    December 28, 2019 / 4:19 am

    I like the blouse, and the handbag, but the Jean’s are not for me, I prefer a dark wash and smoother fit. I would add some jewelry, dark wash or colored Jeans, a pair of flats and be out the door.

  61. Kathy
    December 28, 2019 / 4:15 am

    Yes! I would so wear this, I prefer a crossbody bag, but the color of the purse is great. I’m not sure about the necklace, look forward to seeing what other people say.

  62. LINDA J
    December 28, 2019 / 4:15 am

    I like the blouse because it is soft and not stiff, also because it does not have a traditional collar. Other than my denim shirt, I don’t like to wear collars. The jeans are too baggy and I prefer a darker wash. I don’t like the color of the clutch and I prefer gold over silver. But I do like that this is a simple basic outfit, with just a pop of color, and that it mixes dressy with casual.

  63. Cindy
    December 28, 2019 / 4:12 am

    I like this outfit – simple & comfortable to wear.

  64. Pamela Lutrell
    December 28, 2019 / 3:36 am

    Love the top and would wear it! This is not how I like my jeans to look. I prefer dark denim and a tighter fit. The handbag is nice.

  65. Susan McClelland
    December 28, 2019 / 3:36 am

    I like this outfit and would wear the jeans and the blouse. I love the colour of the purse but it’s a bit big for me and I prefer cross body bags, as they free up my hands and I’m less likely to loose track of it. The blouse is simple but I could also wear it to work – pieces that do double duty are a nice bonus, particularly as I’m transitioning toward retirement.

    • Jennifer
      December 28, 2019 / 12:02 pm

      Great observations Susan. Thanks for sharing.

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