Would You Wear It- Casual Summer Dresses

Would You Wear It- Casual Summer Dresses

Happy Saturday ladies. I went to our outdoor mall yesterday and I was surprised to find it jammed with people. Most of the stores were open and shoppers were walking around with either a glassy look in their eyes or frantic excitement. I found a mannequin for today and returned something I’d bought right before everything locked down. The saleslady remarked that it felt like we had just lost three months. I had to agree.

It’s time for would you wear it. If you’re new here, each Saturday my friend Pam and I share a store mannequin and ask if you would wear what it’s modeling. Stores dress mannequins to showcase their newest merchandise and to give shoppers styling ideas. Some are terrific and some make you question the sanity of the merchandiser.

I like to hear your styling suggestions because we can all find inspiration everywhere. So grab a cup of coffee or tea and lets talk fashion.

casual summer dresses from J. Crew Factory

these are from J. Crew Factory

What do you think? Would you wear these?

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

Here are a few of the weekend sales which seem to get more amazing each week. The stores have brand new collections on the floor that they’ve had to put on sale because their July collections are on their way! It’s bad for the store and great for us.

Ann Taylor: Extra 50% off sale styles.

Chicos: 40% off your purchase with code 29238.

Loft: 40% off full-price styles and up to 70% off sale styles with code YESSS.

Nordstrom: There are always some great items on sale here.

Soft Surroundings: 30% off select styles with code SWEET.

Talbots: 50% off three + items, 40% off two items or 30% off one item.


Now let’s head over to Over 50 Feeling 40 and see what Pam’s Mannequin is modeling today.

Please be kind, be well 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. Brenda
    June 14, 2020 / 5:48 am

    Love both dresses. They look fresh and summery. I’m 70 and I love color. I think 70 is a mind set we ladies think we have to dress a certain way , and wear our hair a certain way. I have purchased several spring and summer outfits that are colorful and very similar to the pictures. I never show my arms so cute sweaters and jean jackets when cooler cover all the problems. During the virus i dress everyday in things I usually wear out. It makes me feel better. Thanks Jennifer for your blog. Love it.

    • Jennifer
      June 14, 2020 / 9:37 pm

      Thanks for being here Brenda! I agree about our mindsets.

  2. Marina
    June 14, 2020 / 5:48 am

    After a second glance, I think the eyelet dress would be flattering. I like the high neckline, waistline and ruffle. Very cool for summer and classic. But no to the color. I’d look like death in all white, plus I‘m a magnet for stains when I wear it! A soft color would be perfect.

  3. Lily
    June 13, 2020 / 6:00 pm

    I like eyelet, but I am too fair to wear that much white. The gingham outfit would look stunning on a tall, tan woman. Alas, I am neither.

  4. Penny
    June 13, 2020 / 2:30 pm

    No I would not wear either one. The black and white check pattern is too much for me, and the style of dress is just not my style. I don’t like style, colour or material of the white dress either. I feel both styles are more for the younger to middle age group. However, I do like both of the hats!

  5. Maggie
    June 13, 2020 / 1:51 pm

    Hats yes! The dresses would look gorgeous on my daughter and granddaughters, but me no😆

  6. Mary
    June 13, 2020 / 1:37 pm

    Years ago I wore those dresses. No need to go back there.

  7. Deborah
    June 13, 2020 / 1:05 pm

    Cute dresses, but for someone younger and thinner. I would need sleeves and I don’t look good in pure white.

  8. Linda Simpson
    June 13, 2020 / 12:43 pm

    I would definitely wear the maxi dress; it reminds me of long summer days from the 1950s. I would wear it to a restaurant (when I venture out again) and even at home when I’m feeling especially fabulous just being me. lol

    • Jennifer
      June 13, 2020 / 8:12 pm

      I love this! I want us to all feel fabulous.

  9. Kay
    June 13, 2020 / 12:37 pm

    I like both of them. I had a white eyelet dress similar to that one that burned up in the house fire. I like to wear maxi dresses around the house in the summer.

  10. Becky
    June 13, 2020 / 11:58 am

    These both get a no from me. The white eyelet dress is cute & sweet, but cute & sweet is not a look I am going for at 65 years old. The black & white check dress is too overwhelming for my short frame.

  11. Elizabeth Day
    June 13, 2020 / 11:52 am

    Although the white is pretty, I would not wear either one at my age.

  12. Dianne🇨🇦
    June 13, 2020 / 11:51 am

    Both very cute & look like summer!
    I don’t do waistlines!
    Love the hat.
    I’m not ready to go to the mall yet.
    I have gone to my favourite little boutique store but we aren’t totally open yet so no dressing up

  13. Nancy Walden
    June 13, 2020 / 10:21 am

    Both dresses look too young for me. I don’t like strapless bras so I don’t buy spaghetti-strapped tops/dresses. The large scale plaid would add visual inches which is something I also avoid. The eyelet dress would look good on one of my 20-something granddaughters.

  14. Nancy
    June 13, 2020 / 10:19 am

    I’d definitely wear the black and white check! And a bra with straps! Add a black, white or bright color cotton sweater or shrug with short sleeves and that takes care of straps and upper arms. Add the hat and it’s a great summer look!

  15. beth byrd
    June 13, 2020 / 10:18 am

    I’d say yes to the black and white dress, but only if it were a shorter length. As is, it would be too much print for my 5’4″ frame. But the dress looks so summery and classic!

    The eyelet dress is pretty, but not something I would wear. It’s a bit too frilly for my style.

  16. Rose
    June 13, 2020 / 10:05 am

    Cute dresses but I must have sleeves also. They really look summery. Nice to see since it’s been so cold here. Not all our stores are opened but can’t wait to go to the mall and feel normal again!

  17. Katrina
    June 13, 2020 / 9:45 am

    Love Buffalo Check, but at my age, it must have sleeves. Sleeves & shorter length to balance the wide shirt. Same for the white dress: sleeves are a must for older ladies. Yes, they both scream “SUMMER!!!”

    • Katrina
      June 13, 2020 / 9:47 am


  18. Robi
    June 13, 2020 / 9:33 am

    Love both of these. Would wear the b/w one in a heartbeat. And just would make the white one bit longer.

  19. Pat
    June 13, 2020 / 8:57 am

    Both are lovely and fresh, but I would pass. The print in the gingham dress would overwhelm me, and the style would not flatter me. I also do not like spaghetti straps. The white eyelet dress is beautiful but is too fussy for my style and lifestyle. I would wear the hat!

  20. Pamela Frazier
    June 13, 2020 / 8:41 am

    I love both of those and the hat! I would definitely wear them. Would probably have to add a shrug to the buffalo check but something light and airy. The white just needs some colorful summertime accessories.

  21. Linda P
    June 13, 2020 / 8:00 am

    I would give the long one a try IF is had straps that would cover bra straps. Being busty, I must wear a bra and hate strapless ones. Also, it looks like the bodice is cut for very small breasts, so it most likely wouldn’t work for me anyway. The eyelet is just too sweet…it would be more appropriate for 20-somethings.

  22. Terri
    June 13, 2020 / 8:00 am

    I love both dresses and would definitely wear the eyelet dress. The long gingham plaid is a younger look and not for me anymore. They are both such a fresh look for summer.

  23. Dawn
    June 13, 2020 / 7:52 am

    I love the eyelet dress and would have worn it in my younger days. It’s so fresh and summery. I recently purchased a white eyelet top and can’t wait to wear it. The hat is great! No to the buffalo checks…too bold for me and I haven’t worn spaghetti straps in years. It would be adorable on both my granddaughters. Happy weekend Jennifer!

    • Jennifer
      June 13, 2020 / 8:05 pm

      Happy weekend Dawn!

  24. Pamela Over 50 Feeling 40
    June 13, 2020 / 7:48 am

    They are lovely dresses…but not for me. It seems I am always writing each week that the outfit would add pounds to a curvy figure…but that is true of these garments. They would not be flattering on me right now.

  25. Cheri
    June 13, 2020 / 7:31 am

    I like both dresses and they would look great on the right body, but not mine. At my age and with my “older” body, I no longer wear clothing that reveals as much skin as the checked dress would. I do like to dress “young” (within reason) and stylish but the days of me revealing a lot of skin are over! Due to my short and busty body I do not wear shirt-waist dresses so I would also have to pass on the white one.

  26. Sherri
    June 13, 2020 / 7:18 am

    Not for me a bit youthful for my age of 70, obviously my own opinion of the style that I could carry off with confidence.

    • Jennifer
      June 13, 2020 / 8:02 pm

      That’s the most important thing, Sherri! Knowing and wearing what makes you feel confident.

  27. Linda
    June 13, 2020 / 7:14 am

    Love both dresses and both would look good on my daughter. For me a dress with a waist doesn’t work. I look for shift or a-line style. I have a Talbots white eyelet a-line in my closet that is at least 10 years old. I’ve worn it multiple times in multiple ways!

  28. Barb
    June 13, 2020 / 7:12 am

    Love the eyelet dress if only it was a V neck and perhaps a little shorter but I would definitely try it on and probably purchase. Eyelet speaks to me for summer! I am petite, so I can see it working well for me.

  29. Cyndi
    June 13, 2020 / 7:12 am

    I like dresses and in previous years I wore them a lot in warm weather months. I’m not a fan of spaghetti straps so I wouldn’t even try the bold gingham. White isn’t a flattering color for me (I’m too fair so I look like a ghost) but if the eyelet dress came in a different color, I would wear it. I do like the hats!

  30. Linda
    June 13, 2020 / 7:11 am

    If the long dress had what I think is called a capulet jacket, short sleeves, short jacket out of an airy material that would blend with this dress, such as white, I would wear it. Without the jacket, no. My arms are not fit enough and it would show my scars on my left shoulder where a horse trampled me when I was 12.

    The next dress I would wear as it is! Both are sweet hot weather choices! Bye the way, I found a pair of summer Sandals that I can wear for short periods so now I don’t feel so self-conscious wearing summer dresses! YAAAAAY!

  31. Janice
    June 13, 2020 / 7:09 am

    I love the white dress and hat, being short it would look great. The black and white needs someone with long legs, and that is not me. The white reminds me of summer days and going out to lunch in the South.

  32. Holly
    June 13, 2020 / 7:01 am

    The black & white check is a hit for me!! Love it!

  33. Elaine @ Following Augustine
    June 13, 2020 / 6:50 am

    No to both of these. They remind me too much of dresses that I wore when I was a little girl and I’d look like a ghost in the white one. The hat though… now that I would love to wear!

  34. Joan
    June 13, 2020 / 6:49 am

    A younger slimmer version of myself would consider wearing these or at least trying them on. But that ship has sailed for me. Kudos to those readers who could wear them!

  35. Bea
    June 13, 2020 / 6:39 am

    These dresses would look lovely on my tall, thin granddaughters! I would consider buying these dresses for them, but where would we go?

    That is the sad question I have for everyone today. I look at my closet full of beautiful clothes and am reluctant to add anything because I am not going anywhere for the foreseeable future. Darn. How do the rest of you feel?

    • Bea
      June 13, 2020 / 6:50 am

      P.S. In case you think I am becoming too negative, I will share that each morning I try to put on a different, more interesting stay-at-home outfit – wearing nicer things that I would not usually wear at home! Maybe that is the secret to surviving these strange times.

      • Cyndi
        June 13, 2020 / 7:04 am

        Bea, I’m your spirit sister on this. None of my ‘better’ clothes are being worn, not even my casual dressy. I do dress everyday (and am requiring myself to wear pants/shorts with waistbands) but 2020 is certainly a different lifestyle!

    • Marci
      June 13, 2020 / 7:07 am

      I agree with everything Bea says! I would add that even thiugh I try to avoid wearing any black near my face, I do love (smaller) black and white checks.

    • Laura
      June 13, 2020 / 8:14 am

      It’s not negative, just realistic. I’ve gone from working in a dressy office to WFH which requires nothing more than a clean t-shirt for video conferences. I’m starting to wonder if I will ever wear my nice clothes again or if it’s athleisure for good! Like you, I try to wear a pretty top and pants a few days a week and find it cheers me up.

    • Debbie
      June 13, 2020 / 9:19 am

      Bea, I feel the same. I feel like I have a closet full of clothes I am not wearing. I categorize my clothing this way: Things I wear at home, with comfort in mind as well as for doing chores like housecleaning and gardening; clothes that I wear to go out for errands during the day (which is not happening much now) and things to wear for going out to dinner or to friends’ homes, as well as vacation and dressier clothes. I pretty much live in the first category. It is a strange situation to be in, for sure.

    • Jennifer
      June 13, 2020 / 7:29 pm

      I’m making myself wear my beautiful clothes. I will not let Covid rob me of their joy!

  36. Donna
    June 13, 2020 / 6:20 am

    I absolutely love the black and white Gingham maxi dress. It screams summer to me, especially paired with the straw hat. You could wear it with black strappy wedge sandals or cognac flats. Pair it with a straw bag and you are all set.

    At first I wasn’t attracted to the whistle eyelet dress. It doesn’t show well in the photo. But once I enlarged it and got a good look at the details I have to say I love it also. Generally not my style with the flouncy hem and crew neckline, but I love the fitted waist and the eyelet pattern so much I definitely would try it on to see how it looks.

    • Jennifer
      June 13, 2020 / 7:28 pm

      Cute styling ideas for the black and white dress!!

  37. Kathy
    June 13, 2020 / 6:01 am

    I would wear both dresses. They are very cute and are perfect for our Florida spring and summers. I’m 68 and don’t think I’m too old for these.

    • Sherry
      June 13, 2020 / 7:00 am

      I agree! Great summer dresses!

    • Jennifer
      June 13, 2020 / 7:27 pm

      You are not too old for these Kathy

  38. Linda V
    June 13, 2020 / 5:55 am

    My somewhat larger body would not look good or fit either of these dresses. If I was much thinner and about 40 years younger, I would wear them! ha ha

  39. Susan McClelland
    June 13, 2020 / 5:54 am

    I agree that these are both lovely summer dresses, but like others, I wouldn’t wear them. A white dress is an invitation for me to spill coffee (or something else that stains) on it. I like the maxi dress and I would try it on to see if it fit. Getting a good fit in this style of dress, in a woven fabric, is a challenge for me, given my narrow shoulders and rib cage. If it isn’t gaping under the arms, the straps are falling off my shoulders.

    Enjoy your weekend.

    • Jennifer
      June 13, 2020 / 7:26 pm

      Happy Weekend Susan

  40. jmp
    June 13, 2020 / 5:45 am

    Both dresses are so cute and I’m a big fan of gingham, but neither dress is my style. I have a friend who they would look perfect on, and I would be very jealous of her when she wore them!! 🙂

  41. MRSBEN2
    June 13, 2020 / 5:35 am

    Speaking namely for myself; since I’ve reached ‘the top of the hill and am mid way going down the other side’, unfortunately a no to both these dresses as far too youthful in overall design. (i.e.: Choice of fabric and style.)

  42. Jan
    June 13, 2020 / 5:21 am

    This display was fun to look at but that’s as far as it goes for me. I don’t wear the sleeveless, fitted waist, flared skirt look any more. My first thought on the buffalo plaid was the popular “farmhouse “ decor that you can see in table runners, pillows or curtains.
    Many ladies will take either of these dresses and create an awesome summer look. That’s why this blog is so much fun. As much as a certain look would not work for me, someone else will love it!
    Enjoy. the weekend!

    • Jennifer
      June 13, 2020 / 7:25 pm

      Happy Weekend Jan!

  43. Lezlie Gravens
    June 13, 2020 / 5:20 am

    Definitely would wear the plaid one! Very cute. Oh, and the hat!

  44. Joyce Reardon
    June 13, 2020 / 5:17 am

    I like them both, but at my age, they look too young. They do scream summer!

  45. Cindy
    June 13, 2020 / 5:15 am

    Neither. The white dress isn’t my style with the eyelet pattern on the bottom. I like the material of the black and white but would pass because of the spaghetti straps. I’m not a fan of strapless bras and never got into the look of showing my bra straps.

  46. Linda GR
    June 13, 2020 / 5:12 am

    Both dresses are very cute. I’d purchase them for my granddaughters. I would, however, purchase and wear the hat attached to the white eyelet dress.

  47. Linda R Gaertner
    June 13, 2020 / 5:09 am

    Both dresses are pretty but I wouldn’t wear them. The checked dress is full right in the area that I’m thick so it would not be flattering to me. I’m not a fan of lace and I’m big chested so the slim straps just wouldn’t work for me.

  48. Cynthia B
    June 13, 2020 / 5:06 am

    Love both of these dresses so much. The white eyelet number didn’t immediately appeal to me, but as I read the comments and took another look, it just captures summer. I bet walking in it with the flounce at the bottom would make you feel pretty! The check dress is divine, but I would wear it shorter than full length…just don’t really dig full length dresses anymore

  49. Susan K Wilson
    June 13, 2020 / 5:02 am

    I would love to wear it. All it needs accessories .

  50. Sandy
    June 13, 2020 / 4:58 am

    I don’t know many over 50 women who would wear either dress. They are cute though. I would love to see cute summery dresses that were mid length with sleeves and youthful. Is that even possible??

    • Jennifer
      June 13, 2020 / 7:23 pm

      I’m always on that hunt

  51. Virginia
    June 13, 2020 / 4:53 am

    I like the look of the plaid dress, but if it’s floor length, forget it! The white one looks like a cute teenager dress. I can’t imagine wearing either look at my age even if I liked it on mannequin.

  52. Connie Haines
    June 13, 2020 / 4:43 am

    Oh, what a cute dress!!! I actually LOVE that strappy buffalo check dress, but understand the comment about wearing a tablecloth. 😂 I think it would be easy to tone down the picnic effect by adding a lightweight white summer cardigan. I also really like the length on this particular dress!

  53. Lori Stewart
    June 13, 2020 / 4:42 am

    I love the black & where checked dress but I am too busty for spaghetti straps. The white eyelet dress is hard to see in the white mannequin. It reminds me of college. I wore a white eyelet Leslie Faye dress at my college graduation in 1982 :). I would give it a try-on to see how it looked.

  54. Jennifer Meschi
    June 13, 2020 / 4:39 am

    I think they’re both too “young” for me at this point. I have always been something of a minimalist and this tendency is getting stronger as I get older. If I wear anything whimsical it tends to be scarves, jewelry or shoes.

  55. Heather
    June 13, 2020 / 4:33 am

    With my pear shape and hippiness the plaid one would not work. Plus at 70 I need a very supportive bra so spaghetti straps are out. Always feel summery in a white dress, so would try that one on.

  56. Leslie
    June 13, 2020 / 4:30 am

    The white eyelet dress is a yes and I would wear some sort of espadrille or wedge sandal, the hat and maybe a jute cinch belt. It’s basically a blank canvas to style any way. The buffalo check is a no for me for so many reasons I will just say…no thanks.

  57. Cindy
    June 13, 2020 / 4:16 am

    If I was going to wear a dress, I’d go for the white eyelet. Everything about it says “summer” to me. I think it looks cool & fresh, perfect for warm weather.
    I wouldn’t wear the black/white buffalo plaid dress. I know many people like this type of plaid, but I feel like I’m wearing a tablecloth. So I don’t wear buffalo plaid in any style or season.

    • Jennifer
      June 13, 2020 / 7:20 pm

      Those kind of pattern associations are hard to ignore. Good to know.

  58. Paulette Levy
    June 13, 2020 / 3:12 am

    Although I like these dresses etc, at my age….sadly, no. When I was younger and firmer (I’m thin but….) they’d both be YES. The black and white shows too much skin for me, personally. The white dress does not fit my taste at all. I want the two hats!

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