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Cute and Casual Dresses for Women Over 50

I love wearing dresses, especially in the spring and summer! I’ve tried on so many dresses 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 cool spring mornings or nights 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 spring and into the summer? I think you’ll find the following posts helpful:

Casual Dresses For Women Over 50 To Wear For Summer

This maxi dress looks so chic and classy. I love how the belt accentuates my waist. You could easily switch it out for another belt, like my favorite raffia ones! I thought the royal blue shade was gorgeous, but you can grab it in seven other shades, including a few pastels that would be perfect for spring. I decided to keep my shoes and handbag neutral to tie in with the raffia belt.

This dress is gorgeous, and I love the colors and print. The twist tie is a cute detail that adds some visual interest. This dress is available in Petite, Plus, and Petite Plus. I love that Talbots is size-inclusive! I added the Top Handle Clutch, which was the clutch I carried the most last year, and I don’t see that changing. I tried on several neutral-colored shoes, but nothing looked better than the navy Azra Suede Pumps.

The colors of this dress are rich and saturated, and the floral print is perfect for Spring. The v-neck is flattering and helps to elongate your neck. It isn’t too low, so wearing this dress to Church would be appropriate. A handkerchief hem creates a lot of visual interest, but it can also be too long. Once I put on the dress, I was thrilled with the outcome. The dress is not tight at all, and I found myself swirling and twirling the whole time my photographer was trying to take a photo. Lol!

I love all of the feminine details on this white belted shirt dress, like puffy sleeves and a fun pom pom trim running along each tier. I ordered a size medium, and it fits really well! I am a big fan of the midi length on myself. It’s not so short that it shows off the parts of the legs that a lot of us are self-conscious about (like cellulite or crepey knees), but it also doesn’t scream Little House on the Prairie, LOL!

I love the tonal print of this dress and the fact that it has POCKETS! This dress looks great with the included belt, but you could also add a white or navy belt to it, and it would be fun to add a red belt for the 4th of July.

This striped classic shirtdress is one that you can wear for years, and it will never go out of style. I tied the belt included with the dress, and tied it in a bow (they are trending), but you could use another belt such as white or maybe a pop of red.

This wavy geometric Wrap Maxi Dress is one of my favorites I’ve styled this year. This is a true wrap dress, and it overlaps nicely. However, anytime I wear a wrap dress, I usually add a safety pin to make sure the top layer doesn’t fly away and give someone the scare of their life. Lol! I ordered a large in this dress, but I needed a medium. The v-neck has a snap closure, which is nice, but I needed to be able to wrap the dress around me more for a tighter fit. A medium would have worked better.

This Boho Maxi Dress is adorable, and it is what I think of when I envision an Easter dress. The color and tiny print are too cute, and it is available in lots of other colors and prints. This is a faux wrap dress. It gives the appearance of a wrap dress, but you don’t have separate layers on the bottom half. This dress takes all the stress (or fun) out of flashing someone on a windy day.

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.

This classic blue & white striped midi dress 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.

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

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.

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 last year. It is flattering and perfect for a beach vacation, but it looks just as cute under a white or blue cardigan.

This dress is stunning! I took it with me when I went to Miami last 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. This pretty shade is no longer available, but I also love the gray-blue and pink-peach! If the weather is cool when you plan to wear this, you could add a pretty shawl to wrap around your shoulders.

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 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.

I was unsure about this halter neck dress 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.

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)

I love a good wrap dress, and this one is no exception. You could wear it to the office, a spring or summer wedding, church, a date night, and so many more places!

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 flat sandal, don’t you?!

Shop More Casual Dresses For Women Over 50:

Are You One Of The GURLS?

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To GOD Goes The Glory!

Verse Of The Day

Galatians 1:10

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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  1. NATALIE K says:

    I like the Navy Polka Dot Off the Shoulder Maxi Dress!!

  2. Lisa Luciano says:

    I am a kindred spirit re: your passion for color! Also love the way you give glory to God! Style and Spirit! Thanks for your fun, whimsical and useful fashion advice for over 50 gals like me!

  3. I am soooo late to the party!!! Love the white dress with black trim! And yes, Easter Dinner is a thing with our family. Everyone comes to our house, my daughter and DIL being a dish and dessert and ham is a staple!
    Hoping your Easter was bright, beautiful, and meaningful!

  4. Maria Vazquez says:

    You look lovely in these dresses. Some of us “gurls” are petite and we know that long dresses only make us look shorter. Can you please feature some shorter dresses for we petite ladies?


  5. Love all your these!! Happy Easter to you and your family!

  6. Is blue your favorite color?

    1. It is one of my favorite colors. My favorite color changes almost daily. Lol!

  7. Ginger Hiller says:

    Thanks for sharing so many great dress options with us! If I didn’t have plenty of dresses in my closet, I would be ordering a few of them. Happy Holy Saturday and Resurrection Sunday!

  8. sue koren says:

    I’m going to need a winter coat over my Easter dress, unfortunately!

  9. Hello! I recently stumbled upon your blog/videos and have been hooked ever since! You show such beautiful clothing and wear them SO WELL! I love the way you put separate pieces together to make a whole look…just lovely. That is something that my 55-yo self doesn’t do so well, but I’m getting better, with your help! I have also been checking out your Amazon store and have found some very useful non-clothing items! I’m not so sure finding you will be so good on my pocket-book though! Hahaha

    Regarding Easter, my family has always gathered for an Easter meal. Sometimes it’s been husband, our kids and me with extended family and other times it’s been just husband, me and our kids. The people and place have varied over the years (sometimes we have been on a spring break vacation with the kiddos), but we have always celebrated Easter with a big dinner.

    Cheers & Happy Easter!

  10. All of the dresses are amazing! Our Easter lunch will be ham, asparagus, sweet potato casserole, green bean casserole, watergate (pistacio) salad, and good old Sister Shubert rolls. We’ll top it off with Wegman’s chocolate pie. I try to do most things that I can make ahead so it’s not too hectic after church when all the kids think they are starving to death and eager to eat. LOL!

  11. Diane Holley says:

    I love all of those dresses. I can’t do sleeveless or very short sleeves anymore. My arms are not pretty!!! I put something on today that was cap sleeves and told myself I had to give it up. As far as Easter dinner you know when my mom passed we sort of quit that. The grandkids are all grown and no one to hide eggs for. Me and hubby will have a quite Easter. Keep the fashions coming just because I can’t wear the sleeveless dresses, I love seeing them. Love your family pictures!

  12. Yes! We always had Easter lunch. Ham, deviled eggs, potato salad, green beans, biscuits and dessert would be our typical menu. HAPPY EASTER ✝️☀️💐

  13. Happy Easter! It is so nice having grown kids that invite us for Easter Dinner – for years I was in charge of it. I love wearing dresses in the summer, and some of these are just my style.

  14. Absolutely beautiful dresses! After years of wearing pants and pantsuits to church (I was the organist and pants just felt better) I have fell in love with dresses again!

  15. All these beautiful dresses are getting me excited about the warmer weather of spring and summer!

  16. Laura Garrett says:

    So many lovely dresses! I especially love the purple maxi. Our Easter menu varies from year to year but must-haves are coconut cream pie and pound cake!

  17. Beautiful dresses!!! Easter dinner, like most holidays in my family, will be at my SILs..she is a fabulous hostess! This year will be. bbq chicken, pilaf, asparagus, salad…Have a Blessed Good Friday🙏❤🙏

  18. Barbara Borkowski says:

    Wow! That’s a lot of lovely dresses. Thanks for doing the hunting for us!

  19. Pam Bowling says:

    We do have an Easter dinner. My mom and I plan it together we are having ham, baked beans, cheesy hash brown casserole, rolls, deviled eggs, and a strawberry crunch cake for dessert.

  20. I can’t remember if my mother cooked anything special on Easter as a young kid. When we were teenagers and young adults, we would have a family Easter celebration. My father would barbeque. Eventually because as our kids grew up and moved and parents gone we just had our own lunch or dinner. Now I go to my daughter’s house. She’s cooking ham and guests are bringing sides like mash potatoes, etc.

  21. Roberta Schwandner says:

    I really like these summer dresses. I look forward the summer to wear some summer dresses.

  22. Pam Bowling says:

    Love the pretty dresses. I love wearing dresses too. Comfy-one and done dresses

  23. We always have a big Easter dinner with ham, rolls, green beans, deviled eggs and all the casseroles: (we live in the south!) pineapple casserole, corn casserole, hash brown casserole) and a spring cake for dessert.

  24. Karen Johnson says:

    The off shoulder polka dot dress is adorable

  25. We always do the traditional ham, or as my daughter used to call it “Easter meat” 😃 with deviled eggs, potatoes, rolls etc. I liked the wavy wrap dress so much, I bought it for myself. I am tall and prefer a midi or maxi dress.

  26. We have ham, hash, brown casserole, deviled eggs, asparagus ( roasted), and rolls.

  27. Love all the maxis. Great for the summer and beach vacations. Great Post. When I was younger I would go to my grandmother’s for Easter dinner after church. My mother still makes Easter dinner. She makes Ham, kielbasa and sauerkraut, hard boiled eggs, and lots sides. We always have a cake shaped like lamb and Easter chocolates. Happy Easter!!!!

  28. B. Robinson says:

    Easter Dinner Menu: ham, mustard potato salad, deviled eggs, relish tray tray, vinegar cole slaw, rolls, pecan pie and whatever anyone else brings that shows up. Sometimes we add chicken and dressing if there are more than 15 coming. It has always been a big deal at my Mama’s house. Then we hunt eggs and fly kites. Sweet memories.

  29. WOW!!! So many cute dresses!
    I have narrowed my list down to 4 favorites. I try to pick midi dresses that don’t have too much flowy fabric because I am only 5′ tall and petite.
    My husband and I will be spending Easter Day going to church and then cooking a rib roast and having a relaxing day.

  30. Beautiful dresses! Happy Easter! 🐣

  31. Oh lots of pretty dresses!!!!!

  32. I’m getting that black and white dress. Love it!! On Easter we always have lunch at my house after church. We have ham, hashbrown casserole, green beans, sweet potatoe casserole, dumplins, and dressing. We have a tradition on Good Friday to get together with the grandkids to make a bunny cake for our dessert. Love our tradition!

  33. We always had a big Easter dinner. My Mom fixed a ham and multiple sides. I have six siblings so it was always a busy time! I’m having ham for Easter, too. It will be just my husband and I but still a tradition.
    Thanks for sharing so many dress options. I love wearing dresses in the summer.

  34. Cathy Carter says:

    All very pretty dresses but that gorgeous royal blue if first dress is my favorite. We have always had Easter dinner in the past…. Ham, scalloped potatoes, asparagus and pistachio salad but this year my family wanted brunch (really breakfast food) so we are having quiche, bacon, baked french toast, sausage and muffins.

  35. Thank you for sharing all the dresses. You look adorable in all of them. And thank you for the verse.

  36. We have always celebrated Easter just like all the other big holidays with a huge family dinner and egg hunt. We have ham, green beans, banana croquettes and deviled eggs, just to name a few of the many things. Lots of yummy desserts and drinks too.

  37. Yes, we have an Easter dinner. I serve Ham and all of the classic “Sunday dinner sides.” We gathered as a family when my children were small, with grandparents, etc. Now, it is whoever can come home for lunch. Sort of a springtime Thanksgiving meal.

    Beautiful dresses!
    Have a blessed Easter with your family!

  38. Awesome post! Happy Easter …

  39. Love all the styles, you give us a great selection! Thanks for all you do for your readers and shoppers! Happy Easter! Yes we do Easter dinner annually, ham, scalloped potatoes, deviled eggs, green beans, biscuits and a dessert, homemade of course.

  40. Patti McDonald says:

    I really like the maxi dresses. My favorite is the wavy geometric wrap dress. I am short and very fair, but it’s nice to wear a maxi and not worry about “pale” legs showing. It was nice to see such a nice variety of dresses and great prices.

  41. You look beautiful in all of the dresses!

  42. I L O V E dresses. I L O V E the Easter service at our church especially when the curtains are closed and no light is shining on the Cross during Holy Week but on Easter while the choir sings building to a crescendo the curtains fly open and sunbeams stream in behind the Cross and cheers erupt (always makes me cry). Then home to traditional ham dinner at our house because we are now the elders🥰. This year our out of town kids are unable to make it so it will be a small but joyous celebration. I am ordering one of the wrap dresses today but deciding which one is almost impossible. Happy Easter!

  43. Phyllis Martin says:

    EASTER DINNER: Spiral Ham, Make Ahead Mashed Potatoes, creamed corn, green beans, deviled eggs, Renwood Mills FORMULA L Biscuit Mix Biscuits. This find has revolutionized my biscuits and dumplings; Key Lime Cheese Cake. Most items made ahead so all family can go to Easter services.

  44. Tanya you look fabulous in that purple/lavender dress. Amazing on you with your coloring!

  45. I love that you list what size you purchased. How tall are you so we know approximately where the dresses would finish?

    1. Faye, I’m 5’6″ tall and usually weigh between 150-155.

  46. I like the striped midi dress with belt

  47. Karen Daniel says:

    I love the selection of dresses. My favorite is the polka dot off the shoulder but Amazon said no longer available. I don’t wear dresses often but when you need one you need one right?!

  48. Love love the dresses. My favorite is the cross halter dress.

  49. Growing up, ham was traditional for Easter. Now, it seems many go out for Easter brunch.

  50. My husband usually smokes a meat and I make sides and dessert.