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. Please!! Enough already with these Prairie type dresses!! in reading the comments I see the petite women hating the length, but I am 5’11”and I just hate all the flounce. It seems to only look good on a very young girl! Where are the dresses for sophisticated ladies that want to be cool for summer and wear a casual dress? That looks sleek!? I also noticed that you were all over the board with the sizing! I’ve been following you for quite some time, and, I know you’re a small, but you had tried on some mediums and even larges! Come on manufactures! Let’s get some kind of Size regulation going on it makes it impossible to order anything online. Also, the two dresses that I liked were over $200. I don’t wanna pay that for a casual dress, but I just sort of like! It would be different if I loved it, but I didn’t love any of the dresses! And it had nothing to do with the model by the way!!😆

    1. I’m praying the prairie trend will pass soon because so few of us want to wear that look.

  2. Thanks for all the dresses! I like the Rail ones too especially the one you ordered. I had to think twice about it because it’s dry clean only. Not sure I want a casual dress like that.
    I can’t do the maxi length being 5′ 4″ and don’t really like the layered tiers. Hope your trips to the dentist are over?

    1. I just have to go back to get fitted for a nightguard, and then I’m done. Whew!

  3. I love the stripped gauze tie front maxi dress on you! Would be great in Mexico trip. I also thought that the Rail blue leopard print was lovely on you. The prices really set me back in my chair! I could make them for $20-30! Depending on the fabric cost. Everything has gotten so costly! I rarely have an opportunity to wear a dress. I did buy that lovely pale grey twist front rayon knit maxi you wore. I will wear it for our 30th anniversary! I hope I look as good in it as you do. We look a lot alike coloring and size however I am 2” shorter. I got it at Nordstrom Rack for a steal compared to these dresses. They are just out of my reach.

  4. Not particularly on today’s topic but … just found out that Nordstrom is closing all of its Canadian stores – the Canadian online store closed today. Hope that means we can shop the US site but no information so far on that. Heavy sigh!

  5. Ive been Looking at chicos dresses with sleeves. Found two i like but waiting for sales as i just dont wear often enough to justify 179-199 for a dress i rarely wear . But dying for a spring dress i can wear with or without a jacket ….. in coastal oregon .. i know chicos sizing works for me . being short and over65. I steer away from midi but a maxi or a knee length works . Thanks for showing us
    Have you ever tried soft surroundings dresses ? I guess they are also mostly online ..

    1. I haven’t tried Soft Surroundings for many years.

  6. I loved the leopard and blue linen dresses. Not a big fan maxi dresses. Too much fabric for me.
    Thanks for trying on all those dresses after a trip to the dentist.
    Regardless you still looked great.

  7. Saw your picture on Tania’s blog, I really liked the flowered long sleeve dress Tania had you try on!! Much different than your usual style. Like you say if it makes you happy and feel good the dress should be yours.

  8. I haven’t worn dresses or skirts for over 30 years, but you have beautiful legs and look great in them. I tough it out even in the heat of summer with full length lightweight jeans or pants that hide my veined “cankles”. I’m always on the hunt for lightweight jeans. Thanks for toughing it out to show us some new styles.

  9. Really like the gauzy dresses and appreciate all the different styles you have given us. Such a great sampling of Spring dresses🌷

  10. In the oppressive heat of southern California, a long, loose dress is more comfortable than close-to-the-body shorts and a tank top. You’ll find me in my dresses all summer long, especially in the evening on the patio when the temperature number drops to less than three digits. Since I lean boho, the tiered and print examples here work for me. I’m short, but no dress is going to make me look six feet tall. Bring on the maxis.

    1. I love maxis. They’re so easy!

  11. I’m not really a dress person either. I think the Audrina is gorgeous but not for me. I might try the Caslon gauze dress in navy. I’m short (5′ 2.5″) but can envision cases where i MIGHT wear it. I have a couple of summer skirts, though, and they seem a lot more versatile. Thanks for the demo!

  12. The rails abstract leopard print blue dress was the winner this round! Glad you bought it – it looked great on you!

  13. Not a big fan of most of these dresses mostly because I’m only 5’1” and long ones even in petite are too long. I really love the short denim with the tucks. It looked good on you, to bad they didn’t steam it prior to hanging it the rack.

  14. Hi Jennifer,

    Not a fan of all the dress, but do love the blue leopard one from Nordstrom. I just can’t see paying $238 for a dress.😐

  15. The Rails dress is great and looks so good on you! Looking forward to tomorrow’s self-tanner post. Thanks for all your hard work!!

  16. The long dresses would overwhelm me at 5′ / 110 pounds / 75 years old. Also, they’d do nothing for me. I get the flow of the dress for cooling but not sure about all that material and the length. Also, wrinkly lol (vs LOL) chicken arms need a 3/4 sleeve. So picky in the name of vanity! My ideal dress for living in Florida is a dress that skims my body with 3/4 sleeves as I don’t want to look like I’m wearing a sack. Admittedly, I’m difficult to please. Love the two Rails dresses. Thank you, as always, for all the choices you give us!

  17. You look great in the dress you ordered. I also like the green gauze, but the back has no “ease” or gathering…but it looks like it has a waist seam in back and that could easily be gathered to adjust the fit a bit. And I so empathize with a rough day in the dentist chair… thanks for your “research” on our behalf!

  18. Wow thanks for trying on all the dresses, especially after being at the dentist! I really like the shorter, more fitted dresses on you. The long ones just have so much material. I like the idea of a long dress because there’s no need to worry about hosiery but being short makes it tricky.

  19. Janice in Ky says:

    Thank you so much for all your hard work. That was a lot of trying on…..usually don’t find that many dresses in one place. I like nearly all of them, was happy to see some sleeves in summer dresses. I would wear most of them, I especially liked the dark blue ones. At 5’ and long waisted I have problems with dresses with defined waist so they would definitely have to be a try on. Just got two dresses from Talbots with 3/4 sleeve for our trip in may. Ordered a pair of the Dr Scholls sandles from yesterday post to go with my new dresses. Thanks again.

  20. I love the idea of dresses, they can be cooler here in SC where we are already using a/c. But I have a difficult time finding something loose but not a tent, in a cool fabric, below the knee but not long, with a sleeve, not a deep v neckline, not a huge print, not tight around the waist and age appropriate (over 70). Thank you for trying on all those different styles, even though we’re not the same shape, it helps to see how they look on you. Looking forward to your research on self tanners.

  21. Bobbie V H says:

    Thanks for the dressing room dresses! I love the one and done idea, cool open sense of skirts and the simplicity of getting back into dresses.
    I am not a fan of the ‘midi’ look; I don’t know how you pull it off so effortlessly since you are petite. I’m 5’4.5″ tall and the midi makes me look short and frumpy!
    One last comment – and I’ve mentioned this before – What is the deal with stores not steaming (ironing) clothes any more? Really dislike the wrinkly look; that’s probably why I’m not a fan of linen.
    Thanks again for the dresses Jennifer. You gave me a couple of ideas for my outdoor, in August, casual, 50th class reunion.

    1. I guess if stores need to cut costs I’d rather it be in steaming than in customer service 😁

  22. The Caslon green with long sleeves has a really nice silhouette. I also like the light blue with long sleeves . I like to roll up my sleeves. These two have a nice classic design, and versatility. I also like shirt dresses generally.

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