Cute and Casual Dresses for Women Over 50 (2025)

Casual Dresses For Women Over 50 To Wear For Summer

Thismaxi dresslooks so chic and classy. I love how the belt accentuates my waist. You could easily switch it out for another belt, like myfavorite 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 myshoesandhandbagneutral 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 theTop 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 navyAzra 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 thiswhite 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 geometricWrap Maxi Dressis 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.

ThisBoho Maxi Dressis 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.

See Also

42 Best Sundresses for Women Over 50

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-dottedOff 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?!

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Galatians 1:10
¹⁰Am 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.