Style + Beauty

Flattering Summer Dresses for Women Over 50 (And Which Style is Right for You!)

May 9, 2024

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If you are thinking that sundresses are just for the 20-somethings, think again. It’s kind of funny, but I never wore them until my 40’s. I was a shorts and leggings kind of girl. Not really sure why, I guess because I was an active mom and always had to be ready to get down on the floor with my little ones, chase them up a tree, or go down the slide at the park. But once my children were a little more grown, I started to experiment with them. Now, they are my signature look for the warmer months.

These summer dresses for women are my picks for the styles that I have found flattering, comfortable, and just super pretty for women over 50, 60, or more. Because we deserve to feel feminine and romantic and beautiful! (But are totally over feeling exposed, itchy, and confined.) Spoiler alert: None of these dresses are over $50!

Note: I only recommend products I would use myself. If you purchase items through the links on my site, I might earn a small commission from the retailer. This is at no cost to you and does not increase your price for the item. Money earned from these commissions helps keep The Middle Girls running! Thank you for your support!

Summer Dresses for Women Over 50

The four types of summer dresses that are perfect for women over 50+:

Summer Dresses with Sleeves

  • Feel less revealing
  • Covers upper arms

Maxi Dresses

  • Full length
  • Adds visual height
  • Covers legs

Midi Dresses

  • Perfect mid-calf length
  • Offers more coverage but shows just a bit of leg

Wrap Dresses for Summer

  • Most universally flattering style of dress
  • For all body shapes


Summer Dresses with Sleeves

Summer dresses with sleeves are perfect as we age because so many of us (me included!) don’t feel comfortable showing our upper arms. Frankly, once you pass menopause, unless you spend regular time in the gym your upper arms lose some muscle mass. Personally, mine can look a bit flabby. But you can still feel cool in that summer sun with short sleeves! They camouflage those upper arms without feeling frumpy. Here are some great choices for sundresses with sleeves for over 50+! Also BTW, since I have sensory issues, I only wear soft fabric dresses because… well, they are soft and they breathe. I have tried to include a variety of body shapes and styles.


Surplice Sundress with Sleeves

This cute maxi dress is so flattering for all body shapes. It’s super soft because it’s rayon, and it has a little stretch to make it super comfortable. It comes in sizes XS-XXL and several different colors. Because it is gathered just beneath the bust, the fabric flows gently over any areas you aren’t comfortable with. This summer maxi dress has sleeves and it’s long enough to drape over your legs for modesty. And, you could even dress it up with a belt, a hat, and some cute sandals! Oh, and it’s under $30!


Summer Dresses for Women Over 50


The Cora T-Shirt Midi Dress

This elegant summer dress with sleeves is a drapey, quality fabric according to almost 100 5-star reviews. It skims your figure without being too loose or too tight, covers the chest for those of us with sun damage, and has a cute little slit at the bottom to give it a little style flair. This comes in sizes XXS to 5X and is in four colors. If you’ve never tried wearing a dress with all-white tennis shoes, this is the dress to try it with! Also great with sandals, or even ankle boots or wedges. Midi length, it shows off your ankles (the thinnest part of your leg, if that’s an issue for you) but keeps your legs under wraps.


Summer Dresses for Women Over 50


Wrap Women’s Summer Dress

This super pretty find is flowy, and soft, and brings out the best in any figure! Wrap dresses are considered the most universally flattering dresses, and this one is perfect! It has a ruffle split hem for a little bit of leg (and sex appeal) but not too much, and comes in sizes XS to XXl. Love. This. Dress! I am partial to the dot prints or the dark green or black myself. You could also belt this one! Surprisingly, reviewers say the polyester fabric feels like rayon and is so soft. This is an elegant summer dress for women over 50+!


Summer Dresses for Women Over 50


Ruffle Short Sleeve Midi Dress

Love this Lady In Red wrap dress from Target. In rayon, it would be perfect for everything from the beach to a dinner out. It would also be beautiful as a summer wedding guest dress! It comes in black too and has a large range of sizes. The ruffles make it romantic and the style and length make it flattering. The split hem visually elongates your legs making you look taller too!


Summer Dresses for Women Over 50


Flirty Summer Maxi Dresses

So if your arms aren’t the (only?🤪) part of you that you want to camouflage, maybe you would prefer not to show off your legs. Maybe this is because you prefer more modest dresses, or because you would prefer to disguise something on your lower half. For me, it’s veins and a little cellulite.  Or maybe you just like the elegance of a flowing maxi summer dress!


Women’s Wrap Boho Summer Dress

Ok, I own this very dress. It is super soft, super flowy, and super cute. The only thing I would caution is that on some women I could see it showing a bit of cleavage. I wear it with a tank or bodysuit underneath, but you could also just pin it in place if it’s a problem for you. Very Boho fun, it’s perfect for the beach, or my personal fav, Palm Springs! I do think it runs a bit small. I am a size 10-12 and ordered a large. Basically, I would order the XL if I ordered it again. (Remember, sizes are just numbers!)  Love this summer dress though! Not frumpy, just fabulous!


Summer Dresses for Women Over 50


Floral Summer Long Dress

This pretty little number has so many reviews calling it flattering, that it hides back fat, emphasizes the waist, hides muffin top… And it’s a romantic and flowing style? It comes in a bunch of colors and prints, my favs are this Blue Dot and the Navy. I have to admit though, I love the Tangerine!


Summer Dresses for Women Over 50


Vertical Stripe Maxi Summer Dress

Ok, this one I love. You might know that vertical stripes are slimming, but it is hard to find clothing that actually has them. This is the summer dress for women over 50, because those stripes are exactly where most of us need them… Our bottom half! It is elegant and sophisticated but also casual and comfortable. I am not a fan of some of the other prints this dress comes in, but these vertical stripes? Yes, please! Did I mention? It also has pockets!


Summer Dresses for Women Over 50


Midi Summer Dresses for Women Over 50+

Midi dresses hit about mid-calf, and are perfect for those of us not quite comfortable with above-the-knee dresses anymore. You can show a little leg while still keeping modest, and show off those cute summer sandals. For me, I still wear some (just) above-the-knee dresses, but something about a longer skirt makes me feel a little bit more like a princess. (Don’t tell my granddaughters, they are the real princesses in my house!)


Flutter Sleeve Smocked Midi Summer Dress

For those of you who love a breathable, flowy dress that isn’t too long and isn’t too short, check out this one. The smocked bodice flatters your bustline but also allows the skirt to fall away from the lower body. Comes in 15 colors and has pockets. I love a white dress. Also, another summer dress with sleeves!


Summer Dresses for Women Over 50


Grace Karin Summer Dress 

This dress is so pretty! Perfect for a wedding guest dress, or for date nights on the terrace of your fav restaurant. The straps are adjustable with buttons hidden in the back. The smocked bodice has good stretch so it adjusts to your size, with a touch of shaping. One reviewer said “This is my favorite dress of all time! “Comfortable, flowy fabric. It comes in 20 different prints, my favs are the small blue print, and of course, this gorgeous floral!


Summer Dresses for Women Over 50


Vertical Stripe Shirtdress

Vertical stripes are visually slimming and this shirtdress has that and more. A drawstring emphasizes your waist and yep, it has sleeves. Made from linen and rayon, it’s a soft but substantial fabric. This comes in solid black and white as well. Very classic and comfortable too!


Summer Dresses for Women Over 50


Gorgeous Summer Wrap Dresses

According to Stitch Fix, (and if you’ve never checked out this personal stylist service, to your door, you should!) wrap dresses are the most universally flattering style for all of us. You can customize the fit around your waist, the natural v-neck is slimming and makes you appear taller, and they are perfect for any age. Check out these super cute summer wrap dresses!


Boho Style Summer Wrap Dress

I own another style of dress in this very fabric and pattern. The fabric is so soft and flowing, and this print… Ah, this print. Love the color so much! It comes in 20 prints and solids. I want to try the navy! If you are shorter than 5’4″, it might fall all the way to your ankles, but still looks great!


Summer Dresses for Women Over 50


Cute Short Wrap Dress

If you prefer a shorter summer wrap dress, this one is super flattering. It has modest coverage, a comfortable fabric, and flutter short sleeves. It ties at the waist on the side and comes in 20 prints and 2 solids, including black. (Which as we all know, is universally slimming.) Over 9000 5-star reviews! Yep, 9 thousand.


Summer Dresses for Women Over 50


Cotton Summer Wrap Dress

This beauty comes in 17 different solid colors. The fabric is soft and flowy and the style is super flattering. It is a cotton/ rayon blend, so make sure to air dry. It has delicate flutter sleeves for more coverage. You can wear it as is, or add a belt. Tie it on the side, in the front or in the back, depending on the look you want. This would look so cute with a straw hat or bag and leather sandals! I love this vibrant tangerine, but also the black, royal blue, sky blue, and pink. Oh, and the teal! And the lavender…😉


Summer Dresses for Women Over 50


These flattering summer dresses for women 50+ are pretty, comfortable, flattering, and affordable. Keep in mind, because I prefer soft fabrics, many of these dresses are made with rayon or viscose. I’ve learned the hard way not to machine dry them… hang them dry and you will be fine though!

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I’m an online educator, business, motivational & mindset coach, podcast host and author helping to teach women over 50 how to empower themselves to create the life they always wanted... 

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