Dressing Room Diary- Casual Dresses

The response to my question about dresses on Monday was a resounding yes, so I have begun my hunt for some wearable, casual dresses for women over 50. I stopped in to do a try-on session on my way home from a particularly tough visit to the dentist. You’ll see one side of my face is frozen solid in some of these photos from that try-on session and others, and it’s not when I revisited the following day.

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 140 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 will tell you what sizes I am wearing to help you understand how things run.


This long sleeve maxi shirtdress has pockets, which is a big plus in my book. It comes in this blue or tan with side slits for ease of movement. I’m wearing a small, which feels large, so I would suggest you size down. It’s a substantial fabric, so you don’t need a slip with this one. It’s available in sizes XXS-XXL.


I wish I had seen this dress before my trip to Miami because it’s great! The fabric is opaque and lightweight, so it’ll be perfect in hot weather. The sleeves are a huge plus in my book, and the front tie gives the bodice some lovely shaping. It comes in a stripe, navy, and this green which is selling out fast in sizes XXS-XXL…I did order the navy for my upcoming trip to visit my brother in Mexico.


This striped dress is a mix of horizontal and vertical stripes in a loose-fitting linen blend. It’s cut on the looser side so that you could size down for a more fitted look. The 3/4 sleeves have a contrasting stripe and elastic at the bottom so that you can push them up. The waist is slightly high but not an empire. It comes in this blue or a white stripe sizes XXS-XXL.


This floral maxi dress is a rayon blend that will be very cool in hot weather. The tiered skirt lays flat rather than poof out because the fabric drapes. The short sleeves have elastic, which I think I would snip and remove. This blue is so fresh and pretty. It comes in sizes XXS-XXL.


This Treasure and Bond dress has vacation written all over it to me. It’s loose-fitting in breathable cotton with balloon sleeves and a ruffled hem. The fabrics have definite boho vibes, which would work around town or in a tropical climate. It comes in sizes 00-18.


I loved this dress on the hanger and even more on my body. This small was too snug for me, so I ordered the medium because they seemed to be selling out fast. It has a gently fitted bodice with a drawstring tie at the waist and rang every bell for me. The sleeves are fluttery but not too girly, and the ruffle at the bottom is soft and not obtrusive. It’s a print I happen to love, and that’s saying a lot because most dresses are florals, and I haven’t gotten comfy wearing them (yet). I plan to wear it with both blue and white denim jackets until the really hot weather hits, and then it’ll work perfectly on its own. I may get it hemmed an inch or two when it arrives because it’s meant to be just below the knee. Yes, this is a splurge, but I seldom buy dresses and have been wanting one. OK, back to the DRD for you 😊.


Here’s a terrific little linen dress with a pin-tuck pleated bodice and short sleeves. The pleats give it some shaping without being snug. The linen is substantial, so you won’t need a slip which I also appreciate in hot weather. It comes in sizes 00-20. I love the drape of this fabric, and the length is really nice.


This mocked dress is in a breathable Tencel/linen blend. It’s unlined but opaque, so a slip would be optional. The 3/4 sleeves have elastic at the bottom, which I pushed up. I’m seeing a lot of dresses and tops with this square neckline this spring. It has side pockets which is always a plus in my book. This dress comes in sizes 0-14.


This dress seems to be selling fast because the only sizes left in my store was XS and L. This is large, and you can see the extra fabric on the hips, so I need the medium. I love the color and unique plaid of this. It’s the sort of dress you could dress up for a shower or wedding and dress down with flat sandals and a cardi. It’s a rayon blend that drapes nicely. It comes in sizes 00-16.


This shirt dress also comes in white, but I decided to try on this fresh, fun green which is trending for spring. The bodice is fitted, which is a nice option and gives you some shape plus, the notched collar adds a bit more structure. This is 10% cotton and comes in sizes 00-18.


Another spring/summer dress with a fitted bodice and ruffled bottom. The straps are nice and wide enough to cover your bra straps. It’s a rayon/linen blend that buttons down the front and comes in sizes 00-18. It’s got a very nice shape, and I’d likely wear this with my Nic+Zoe cardi for some arm coverage.


The dress is clean, but the mirror obviously has some schmutz on it. This gauze dress comes in 3 colors in sizes 00-18. I think this would be fun with a belt, make a great bathing suit coverup, and just be cool in hot weather. It’s machine-washable, 100% cotton, so perfect for hot summer days.


This dress is way too snug on me, but I managed to button it to show you how it looks. It’s got long sleeves with smocking on the cuffs. I would call these 3/4 sleeves, not full-length. It has a ruffle on the bottom and is a floral print. It has a drawstring waist, with buttons up the front, and comes in sizes XXS-XXL.


I spotted this matching top and skirt that looks like a dress when you tuck the top in. Nic+Zoe is showing a lot of large florals for spring this year.


Bad angle for a photo of this dress because it’s not as long as it looks. I love the fresh blue and white stripe in a crisp cotton that has a lovely polished finish. The side ties snug the waist all the way around. The V is modest, and the length is 48″. It comes in sizes 00-16W.

This is my first run at dresses for you, and I’ll have more in the future. These photos remind me of how important self-tanner is for my legs. I’ll have a roundup of some of the best self-tanners and leg makeup for mature skin on the blog tomorrow. And yes, “hose” is back for spring/summer 2023, but I won’t be wearing it when it’s blistering hot.

Thanks for reading, and be sure to wear what makes you feel confident.


  1. Thank you for the dress review. At 5’2″ the long dresses are not for me. I did like the shorter styles. I will be looking.

  2. I did like the small blue print you ordered in the medium. The rest I could not see wearing. I have 3 simple maxi dresses and haven’t worn since before Covid. I just don’t seem to have events where I choose them over nice pants and a dressier top.

  3. Thank you for all your reconnaissance! You have stamina! I’m trying to decide if dresses for summer days are for me. Life in a northern state does make a difference. I’m tempted by the “one and done” ease. My mom wore dresses nearly every day of her adult life until she retired. In my mind, that is still how I see her. I have only two casual summer dresses. One is an Eddie Bauer knee length sleeveless dress with a crossed bodice in a fabric I love, but I had to shorten the shoulder seams to fit. I wear a light sweater with that one to cover my arms. I have one short light blue pullover linen dress with loose sleeves but don’t wear it much. During your “fashion show”, I put a couple in my Nordstrom cart, but need to contemplate… I ordered a knee-length black cotton dress with cap sleeves from Anthropologie last week, so I’m willing to try. I appreciate your post.

  4. I think dresses that have ruffles, flounces, gathers, big prints, etc. , do not flatter at my age and height( 5’2″). I would have to try on for sure.

    Do you have a Talbot’s near you? I would love to see you model some of those dresses.

  5. Thank you for sharing all of these dresses especially when not feeling 100%! I usually give up on all the dressing & undressing after just a few trys! I’ve been on the hunt for dresses as I’m planning my cruise wardrobe & I like the idea of one & done dressing. I actually have that green gauze dress & love it! Quince makes a linen dress very similar to that Faherty one which I love on you ❤️

  6. Thank you so much for this dress sampling. As a short, petite person I avoid the long flowy dresses. My ideal would be a cotton shift dress that comes just below the knee. A couple of these dresses fit the requirement.

  7. I love the maxi dresses but at 5’1″ it seems to make me look shorter.
    The blue linen Gemma is exactly what I have been looking for , but in cotton
    gauze. Linen is so comfortable but it gets wrinkled too easily. Too bad they can’t make linen wrinkle free. But I loved this post. Thanks Jennifer.

    1. Chico’s makes a wrinkle resistant linen

      1. Frances B says:

        Chicos makes wrinkle resistant shirts but not dresses. They are not offering tops in Petites now. They have some petite dresses but most of the styles offered are now just pants and jeans. You may be able to wear their regular misses tops because you describe yourself as having broad shoulders, long arms, and are long waisted but at 5’1”, I need tops that are truly scaled for petites with narrower shoulders, higher armholes, shorter sleeves, and shorter length. Too bad Chicos has chosen to ignore the wardrobe needs of their petite customers.

  8. I too have a very hard time finding a dress that is casual and age appropriate. I tried on a dress like the fist green one and just didn’t like how the ties came off the chest instead of the waist. Looked weird to me. If anyone finds knee length casual dresses somewhere, let me know!

  9. I’ll be the first to give you a shout out, Jennifer, for braving an after dentist try on to show us what’s out there this spring. However, I’m with suzanstew – can’t really go with a long dress for casual every day wear, nor for outings. At 5’2″ and over 65 it makes me feel like the dress is wearing me not me wearing the dress. And having elbow length sleeves is a must have with wrinkly arms at my age. Don’t mind long sleeves as long as they can be rolled up as it’s pretty darn warm here in SE FLA.

  10. Love the striped gauze shirtdress & the leopard. Nice to see how the pintuck & tiered look on someone else – now I know why I buy & give away. Hope you are feeling better

  11. Sandals and summer dresses, especially ones with pockets, are my favorite outfit so you’re showing me all my loves this week. The first and last striped dresses are my favorites along with the patchwork dress. I think all of them would require a try on first. You’re a lot more patient with trying on items than I am!

  12. I just love love that flowered dress on you and the one you tried on of Tania’s —- you need color girl and those dresses look amazing on you!

  13. Thank you for letting us see what dresses look like on a woman of a certain age!

  14. You look great, even with a frozen mouth, LOL. This post shows how hard it is to find a cute casual dress for older women. I love dresses, but it can be difficult to find one that doesn’t look like it’s for a young girl. I really like the “baby doll” stripe dress, but is that too young for older women? What do you think. I also love the Caslon floral, but is the bottom tier ruffle too young as well? What do you think about that. Love the leopard on you. Thanks for doing this, when I’m sure you were not feeling your best.

    1. The baby doll stripe would work at any age, if you like the shape. I like the Caslon floral because the fabric was so nice, not flimsy.

  15. suzanstew says:

    I like a few of the dresses – the Rails ones seem OK and the Faherty linen dress. But I simply can’t get into this floor-length maxi dress thing. This post caused me to look and I do see that my beloved Talbots has a few of these long voluminous things, but not a lot. Maybe I can’t see myself in any of this because (1) I am an old, overweight person and (2) I live in a place where all I can think about right now is keeping warm and thin cotton dresses don’t do it for much of the year, but I wish this trend would go away! But it is a great post showing such a wide variety of dresses.

  16. Thank you from a summer dress person! I love the blue Rails print you ordered; have something similar from last season that I love. It will look great on you. The Faherty linen looks tempting, as does the Nordstrom stripe at the end of the post. C’mon summer!

  17. Great post as I am shaped like you it is most appreciated loved the range of colours too and the different lengths happy to hear you are to have more dresses coming thank you

  18. I love a breezy dress in the summer. But I am not a fan of tiers and ruffles. It is hard to find unruffled clothes right now!

    1. I was going to say the same thing. Why break up the line of the skirt with a ruffle at the bottom?

    2. It’s very hard to find dresses without tiers and ruffles these days. The trend can’t pass fast enough for me 😁

  19. The Rails abstract and shorter Caslon floral look great. The others are not dresses I would wear at any time, especially in the summer. The amount of fabric (lightweight or not) and/or the prints is overwhelming.

    Thanks for your efforts to find dresses for those of us who love them!

    1. I totally agree. I am 5’2” and cannot wear the long or ruffled dresses . I think I would look like Little Bo Peep! Love the Rails dress.

  20. I hope you are feeling OK today after your trip to the dentist. You are trouper to try on all these dresses with a frozen mouth. I really like a couple of the shorter length dresses on you. The Abstract Leopard Print Dress is lovely and looks wonderful on you though its pricey for a “casual” dress. The Calson Floral Sleeveless Dress looks nice too. I’d wear either style to church in the summer. Church is the only place I wear a skirt or dress anymore. The longer dresses don’t appeal to me at all. Maybe the baggy dresses are comfortable in tropical climate but I would never wear one. A couple of them would be really cute shortened but the “granny” dresses scream “old” to me.

    1. I agree with you Jan. Those long dresses in pale colors are not for me. That was a lot of work trying all those dresses on and I do appreciate seeing other on a real body.

  21. Wow! I am a dress( and skirt ) fan. My warm weather go to. I like tea length/ below the knee and need to start the self tanner soon! When you mentioned slips it occurred to me I haven’t worn one in years! Also, never going back to pantyhose… black tights maybe but never hose again.
    Thanks for the DRD and look forward to more.

  22. Jennifer, the striped gauze dress looks fabulous on you! Your hair and coloring looks great with it! So many dresses! Wow!

  23. As my legs are definitely not my best feature, I tend to avoid them. That being said, I can appreciate the ease and coolness they would offer. The fabric and print make a HUGE difference in the look and the “lay” of some of these dresses

  24. Thank you for doing the hard work….I wear dresses in summer and a few of these dresses look amazing on you and especially liked the Carslen sleeveless floral, the Rails Audrena, Faherty shirtdress, Rails abstract leopard, and the Treasure and Bond. Actually more than a few. 🙂

    1. I have the Faherty in my cart while I think about it. They have such nice fabrics.

  25. I love the Rails dresses and also partial to the shorter styles. Nothing is better to me in the summer (living in the South) than to throw on a dress and sandals and run out the door for errands and lunch. It’s cooler and more flattering on me than shorts.

    1. I’m not a shorts wearer so dresses would be it in the hot weather.

  26. Elizabeth A says:

    I prefer the shorter dresses over the maxi length. I am 5´. I agree – florals can be a bit much and your splurge dress is very similar to something I have been looking at online. For those of us over 65, this is reliving the decade of ´66 – ´75 with the ´peasant´ and empire waists with the shirring (?) on the top. I wear a lot of dresses, and I rule out all dresses with ruffle on the bottom as I think it makes my look choppy with my short height. Also, I will spend a bit more if I am on the fence about price (always on a budget) if a dress has pockets! 😍 pockets!

    1. I love pockets too!

  27. Did you order the dresses and have them sent to your local Nordstrom or Nordstrom Rack? My local store never has a good variety of dresses.

    1. No, but you can do that. I visited two different stores.

  28. The last one is the clear winner in my book… in fact it looks way better on you than the model! Cool, comfortable, and a flattering color. Thanks for the effort of trying so many on for us to compare.

  29. Oh my — best keep looking.

  30. I do like the shorter dresses ( not the granny length however) , but not to run out to buy- I’m just not a dress person I guess.

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