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Cute and Casual Dresses for Women Over 50

I love wearing dresses, especially in the summertime! I’ve tried on so many dresses in 2023 that I wanted to do a roundup of cute and affordable casual dresses for women over 50 that you’re going to want to add to your cart. There’s a dress in this try-on for everyone because I made sure to include a variety of lengths, necklines, and silhouettes. A lot of these dresses will be perfect for transitioning to fall under a cardigan, denim jacket, or moto jacket! Let me know your favorite in the comments below!

Are you looking for items you can wear throughout the rest of the summer and into this fall? I think you’ll find the following posts helpful:

Casual Dresses For Women Over 50 To Wear For Summer

1. Tiered Maxi Tent Dress

I’m partial to midi and maxi dresses because they make me long and lean. I am 5’6″ tall for sizing reference. This turquoise blue tiered dress is perfect for summer since you’ll get a lot of air flowing up the dress. It will be easy to transition this piece into fall weather by adding a lightweight cardigan.

2. Blue and White Fit and Flare

This blue & white striped midi dress is classic looking and would look great dressed up with a blazer. The dress has an elastic waist, so I added a stretchy belt to the look that coordinates with the crossbody handbag.

Square Neck Shirred Maxi Dress (Large) || Linen Blazer – White (Size 10) – (Similar) || Top Handle Straw Clutch – Tan (Out of stock – Natural is similar) || Clear Two Strap Wedge ( Sized Up – 9.5) || Beaded Hoop Earrings || Set of 2 Chain Necklaces in Gold

3. Square Neck Maxi Dress

Look at the gorgeous print on this dress!!! I wore this dress under a blazer which will be great for fall, but it looks just as beautiful without the blazer for the rest of the hot summer months.

4. Off-the-Shoulder Polka Dot Maxi Dress

Y’all, I love this navy polka-dotted Off The Shoulder Maxi Dress!!!  It makes me feel so pretty, and isn’t that the goal of our clothing? It should make you feel like a million bucks when you put it on, and this one sure delivers. The dress is lined about to my knees, so there is no need to worry about it being see-through. It is very comfortable, and I love the way that it fits. You could wear this anywhere you want, but I think it would be great for a cruise, reunion, wedding guest, or to a friend’s house.

5. Smocked Midi Dress

I think that colorful must be my middle name, so you know I love this dress! I wore it when Joe and I went to Mexico in March. It is flattering and perfect for a beach vacation, but it looks just as cute under a white or blue cardigan.

6. Lace V Neck Maxi Dress

This dress is stunning! I took it with me when I went to Miami earlier this year. It’s a little too formal for regular day-to-day wear, in my opinion, but it would be so beautiful to wear as a wedding guest. I grabbed it in this pretty shade, but I also love the gray-blue and pink-peach! If the weather will be cool when you plan to wear this, you could add a pretty shawl to wrap around your shoulders.

7. Halter Neck Floral Backless Maxi

I LOVE the colors of this dress! It’s so happy and fun and was one of my favorites that I took with me to Miami. You’ll definitely want to grab some of the silicone coverups to wear with this one because the back prevents you from wearing a traditional bra. This would be beautiful to wear to a vacation or a wedding. I think this would be super cute paired with a denim jacket, as well.

8. Crossover Halter Neck

I was unsure about this one when I saw it online, but I loved it so much that I thought I would take a chance and just order it! Luckily, it’s gorgeous and looks much more expensive than it is. It comes in several other colors and patterns, but I loved this floral magenta! This is another one that you can’t wear a traditional or even a strapless bra with, so you’ll need these.

9. A-Line Casual Dress

Every woman should have a little black dress in her arsenal. They are great for literally everything from work, to church, to funerals, to going out to dinner, and beyond! Accessories are your best friend at dressing a dress like this up or down, depending on what’s on your social calendar for the day. This material is very forgiving as it’s a little thicker, and the fit and flare silhouette is always a favorite of mine. This dress runs small; here is where you can see me wearing it in a size XL. (Scroll to the 2nd outfit to see the dress)

10. Floral Wrap Maxi

I love a good wrap dress, and this one is no exception. I could see wearing it to a fall wedding when it’s still super hot outside.

11. Floral Boho Dress

This dress has a little bit of a 70s vibe to it that I can’t get enough of. It hits just at the right length on me. Plus, I love that you can wear it on or off your shoulders. I think it will be just as cute with a boot this fall, don’t you?!

Shop More Casual Dresses For Women Over 50:

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Verse Of The Day

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10 Am I now trying to win the approval of human beings, or of God? Or am I trying to please people? If I were still trying to please people, I would not be a servant of Christ.

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56 Comments

  1. Love, Love, Love all of the dresses Tania!

  2. Jostar Online says:

    I found this article really informative and you have mentioned some amazing facts. I will bookmark your site and keep checking for more of your amazing articles. I would like to thank you for the efforts you have made in writing this amazing article.

  3. Sandra Johnson says:

    I love all the dresses you showed in your blog. Trying to see which one for complement my body type. I am a young 75 year old. Thanks for all the advice you give. Love. Sandra Johnson

  4. Tania;
    love that red dress on you. don’t think I could do the peep hole, but you’re rocking that dress. Question, do you ever wear a white jean jacket? just curious your thoughts on a white one. thanks!

    1. Shar, I love wear jean jackets, and I’ve tried to find a white one that fits me correctly. So far, every one of them fit weird. I need to see if my favorite one from Amazon is available in white.

  5. Katherine says:

    I really like the blue/white fit and flare and the boho dress. I prefer short or midi dresses. Maxi is too long for me. And…I may be the only one who thinks this,but the crossover halter dresses don’t do anyone’s boobs any justice!

  6. Tania, those two halter top dresses look fabulous on you. I am very glad you showed them, and it’s good to see all these, thanks.
    Have fun with your family; you are so blessed, not all of us can get our families together.

  7. Oh how I wish I was taller! You look great, but those dresses would sweep the floor on this 5’2″ body!

    Enjoy your parents’ birthday celebration!

  8. Tania,
    All these dresses are beautiful and they look great on you. The problem I have, is that I am petite, 5’2 and in the description, they never list the length of the dress or the sleeves. it makes it very hard for me to order online.
    I hope you enjoy your time with your family. I live in the Nashville area.
    Love Tennessee.

  9. I love wearing dresses especially here living in Florida. So much more comfortable than shorts. It’s hard to choose just one because I would so wear them all

  10. So many cute dresses for every occasion and so reasonably priced. Thank you for showing these dresses and the wonderful accessories. My favorite is the polka dot maxi.

  11. You are made for color! Love the dresses especially the light blue/green one.

  12. #11 is my favorite (I’m a 70’s girl!) Thanks for sharing so many dresses this summer! My parents are both alive and well, but they moved from the house we grew up in so it isn’t the same when I visit. Have a wonderful time!

  13. Love the dresses. Just wondering what bras you find that work with these dresses? The traditional bra keeps me bound to the traditional shouldered dress.

    1. Nora, I’m not huge chested, so I usually use just wear the silicone covers.

  14. can you find some wrap dresses that stop at the knee and are decent for worship at Church?

  15. So many cute options detailed here! I have two summer weddings and several of these would fit the bill!
    I especially love the navy dot maxi ☺️

  16. Jessica Small says:

    The dresses are beautiful. However, for a women who are 5ft tall cannot wear this style of dresses. Have any styles for short/petite women?

    1. Jessica, I have more dresses coming up soon.

      1. Dresses for shorter women, thanks..

        1. Haha! I just commented back to another lady that I was looking for shorter dresses since I tend to style mostly midi and maxi lengths.

          1. Do you have a Talbots or Talbots Outlet near you.
            They carry petites (for women 5’4″ or under) and have darling dresses!

  17. The fragrances! As I entered my 60’s I’ve become allergic to those smells. My office placed these little toaster sized scent dispensers around the building – behind furniture in the corner, someplace unnoticed and every couples of minutes or so a little shot of fragrance was sprayed into the room. The idea was to create a “brand” smell for your business, we were told lots of hotels do this. Within an hour of being in the building my eyes & throat were burning, my sinus were running, the headaches started. I learned that the fragrance was a chemically created mixture – no natural oils. I couldn’t function. The devices were unplugged. I wouldn’t be surprised if that is what you experienced as well.

    1. Diane, I’ve also noticed that certain scents don’t bother me. More expensive perfumes don’t bother me; it is usually the cheaper ones that give me a headache. I told my friend that I thought it was because they use the chemicals instead of high-quality oils.

  18. Love – love – love that first maxi dress. #6 is also gorgeous.

  19. Jayne Finkbohner says:

    So sorry your not feeling 100% at your gathering. Nothing worst than an ongoing smell that nails you!
    Love the dresses and can’t wait to see what you share when you get home.

  20. So many great dresses! Thanks for sharing!

  21. Christine Clementi says:

    Thank you for this post! I have three dresses in my cart from Amazon. I not only love the dresses but the prices, as well.

  22. Love all the floral prints! They scream spring!

  23. Roberta S says:

    I love the long dresses especially the polka dotted ones.

  24. I have ordered from some of these places in the past. Great value and looks. Thanks.

  25. Love the dresses. I just want to know how many suitcases are going with you to Miami???

    1. I took 2 large suitcases with me. 🤣

  26. Especially love the polka dots!

  27. Thanks for this post. There are a couple of dresses here that I am adding to my wish list.

  28. These dresses are so cute!! Which, do you think, are appropriate for a woman of mid-sixties age? I always fear I’m dressing too young. I certainly don’t feel “elderly”, like I read I am ☹️ 😂 I refuse to dress like an “old lady”, though. My sweet mama, who was almost 100 when she passed away, wore skinny jeans, an embellished denim jacket, tunics, tees, not all at the same time, of course, right up until the last. She was a style icon at 4’10”!!

    1. Delaine, I’ll be 63 in May. Don’t let age keep you from wearing what you like.

  29. These dresses are great and so reasonably priced especially if you end up wearing the dress only once. Thanx!

  30. Tania, THANK U for this post!!! U r the absolute BEST!!!!! I just purchased several. I’m praying the lace, blu/gray is going to b exactly what I’ve been looking for-for Easter! That color is stunning!!!! Thx again!<3

  31. I love them! Now to decide which ones will make it to my closet🤔

  32. Wendi Guenterberg says:

    Love these cute spring dresses!

  33. Love the dresses. Quite a collection covering all kinds of occasions.

  34. These dresses are beautiful but I cant wear dresses because of a disability. I need something g dressy for a graduation that is not a dress if you could do a post on that.

    1. Linda, what are you looking for? Maybe a pantsuit?

  35. I love these dresses! However I am only 5’3″ and these would be to long for me. I do love A- Line it’s my favorite style. I am needing lots of dresses for this Spring. You look beautiful in everything! Praying for your safety as you travel home.

  36. Thank you so much for the dresses, it’s just what is needed to keep the Spring/warmer weather dream alive, when our weather is going from sunshine and the 60’s to dark and rain. I have at least one of your recommendations in my Amazon cart. Have a great working vacation.

  37. Crossover halter neck – the headlight flowers? Does your dress feature that?

    1. Lol! That made me laugh so much! I brought that dress with me to Miami, so You’ll see photos of it soon.

  38. Lois Munn says:

    Enjoy your blog! Would love links to petite sizes.

  39. Rosalinda Salcedo says:

    Love all these beautiful dresses!! So many beautiful options!! Hope that your trip gets better!! Have a great Thursday!!

  40. Cute and very affordable dresses. I have one of the PrettyGarden dresses and love it!

  41. Mary Kinard says:

    I am a big fan of the polka dots!

  42. Love them all! My absolute fact was the off the shoulder maxi dresses. Can’t wait to see you in them.

  43. Thx!! Cute! Any petites?

  44. Love the very first dress in your listing of dresses. I see there are many color options, thinking the one you chose is the prettiest. Thank you for doing the legwork to find all of these gorgeous dresses.