Best Flattering Summer Maxi Dresses for Women Over 50
When it comes to timeless style, few things are as effortlessly chic—and forgiving—as a flattering maxi dress. For those of us over 50, it’s all about feeling confident, comfortable, and pulled together without trying too hard. Great style doesn’t have an expiration date, and the right maxi dress can skim in all the right places, and still feel easy and fresh for your summer event. Let’s chat about the best flattering summer maxi dresses for women over 50.
My daughter Jenna and I at a friend’s wedding. Jenna’s dress was purchased at the Sundance Outlet. You can find one here on Poshmark here, here. I am wearing a no longer available Lily Pulitzer dress similar here, and here.
Best Flattering Summer Maxi Dresses for Women Over 50
What Makes a Good Maxi Dress for Women Over 50
Mature women need to choose carefully and wisely (I have learned this one the hard way). Focus on the right fit, flow, and fabric. Gauze, linen, linen blends, and poplin styles are cooler than synthetics. Bold floral patterns may not be your best friend.
This beautiful embroidered dress from Sezane was a little out of my (lack of pattern) comfort zone, but it was so beautiful I couldn’t resist. The embroidery is exquisitte. It can be worn now and into the fall.. Bag is Mar Y Sol for Eileen Fisher. Sandals from Camper as above. This dress would be lovely for a summer wedding.
Best Styles for Different Shapes and Sizes
Pick a flattering silhouette for your particular body type.
Hourglass
Hourglass shapes have a well-defined waist, a full bust, and full hips (that’s me). Flattering styles include wrap dresses, sheath dresses, fit and flare options, dresses with a bias cut, or a peplum option. These styles highlight your natural curves and accentuate your waist.
I purchased this gauze shirtdress from Nordstrom last year (no longer available), but this dress with the nipped in waist looks amazing. If they have your size it is $45) Loft has a similar one in an even prettier green here.The sandals are from Camper here., and the bag Marysol here.
Inverted Triangle
Inverted Triangle shapes have wider shoulders and busts with smaller hips. Flattering styles include a-line, empire waist, and dresses with a fuller skirt or ruffled hem. Choose necklines that balance the upper body (like scoop or v-neck). These styles add volume to the hips and balance the proportions.
This Mersea Ibiza caftan dress in a beautiful shade of green could be dressed up for day with their go-lightly wrap and dolce vita sandals (on sale) or worn as a swimsuit coverup. Excuse the blurry photo.
Pear Shape
Pear shapes have wider hips and thighs than shoulders. Flattering styles for pear shapes include a-line dresses, empire-waist dresses, and dresses with details or volume on the upper body, like ruffled details or embellished shoulders. These styles balance the proportions by focusing on the upper body and downplaying the hips.
I love this beautifully embroidered maxi from Boden. I would probably wear it with simple sandals and let the dress be the star. Here I am sharing it with my favorite sneakers, and the beautiful baseball cap gifted me by Chord here.
Rectangle Shape
For rectangle shapes, shoulders and hips are relatively the same width. Flattering styles include wrap dresses, a-lines, empire-waist dresses, and dresses with waist-defining details like belts, ruching, etc.
Round Shape
If you have a round shape you are curvy through the midsection with a less defined waist (hello menopause). Empire-waist dresses, wrap dresses, a-line ,fit and flare dresses and shift dresses flatter. These styles skim over the dreaded belly, define the waist, and create a long, lean line.
Petites
If you are a petite size (generally) you should avoid overly long, billowy, loose-fitting, or overly patterned options. They can add bulk and make you look even shorter. Midi dresses often work on petites. A floor-length style can be challenging.
This dress from Mersea would be a midi on anyone tall. I adore the color of this dress. This dress on me without a belt would be too much fabric, but I love it with a belt. Sandals are from Dolce Vita,, hat is from Helen Kaminski (think price per wear; her hats last for years), and the bag from Mersea.
Talls
Tall women can absolutely rock a maxi dress—just be mindful of the length. Ideally, the hemline should hit at the ankle bone or slightly below for a truly flattering look. On taller frames, many maxi dresses tend to run short and look more like midis, so it’s worth checking the measurements or opting for tall-specific sizing when available.
Considerations
A summer maxi dress or midi dress can camouflage a multitude of sins at our age. I am afraid sleeveless, flutter sleeves, cap sleeves (never good on me even when younger) days are over (not for everyone, many can still pull it off). My upper arms are not that attractive. I prefer elbow-length sleeves. I am not a huge fan of floral dresses (though I love them on others)
I purchased this Xirena dress last summer. I don’t normally go for pattern, but I loved the batik inspired print of this dress and the flattering fit. I wore it over and over. I like this years version of this dress as well.I am wearing it with a favorite hat and comfy sandals from Eric Javitz on sale.
Wardrobe Warriors-Dresses to Wear Again and Again
I try not to buy anything unless I can wear it muliple ways on mulitple occassions.
I wear this Quince dress as a coverup or belted for a day out. It is a wardrobe warrior. I love a dress that wears “several hats”. I would also pair it with sneaks and a baseball cap for a trip to the farmers market.
I own the Frank and Eileen shirtdress in chambray and white. It is definitely a wardrobe hero in my closet. You can see how I style it multiple ways in the post I did with Kim for Signature Style here 15 ways to style a white shirdress at any age here.
This new to me company Heidi Houston (out of Texas) shirt dress is another one that could be styled with olukai sneakers & an open weave sweater from Splendid, as I did here, or sandals later in the summer. Love the sleeve length an the crisp poplin fabric.
Maxi Dresses (most on sale) that I am Loving
More of my favorite dresses in my shopmy shop here:
Why Maxis Can Work After 50
Let’s face it— in the warmer months, there’s something incredibly appealing about the simplicity of a one-and-done outfit. A great maxi dress takes all the guesswork out of getting dressed while still looking polished and a touch of sophistication. Opt for breathable fabrics, natural or lightweight fabrics like linen or cotton gauze; they offer breathability and coverage, keeping you cool and comfortable without sacrificing style. Whether you are heading to a special event, a summer wedding, a beach vacation, wine tasting, multiple baby showers, or just a casual outing for the summer months, there is a perfect summer dress for you.
Thank you for reading the Best Flattering Summer Maxi Dresses for Women Over 50. You might also enjoy my post 12 Curvy Maxi Looks for Women Over 50 here. How do you feel about maxi dresses? Do you love them or loathe them? Now let’s pop over and visit Kim to see what she is sharing:
northern california style
Cindy –
A great post that I just read – I was away when this posted.
I LOVE that blue Boden one! I think dresses are much cooler than pants in the summer, and if you have any leg issues, maxis are great! Love you in that Sezanne dress – you look gorgeous.
Cindy, you look beautiful in all of your picks. My favorite though is the blue Boden dress!
I am a dress girl, they are the hero of the closet because of the ease of dressing. You can dress them up or down and always look great.
Have a wonderful week.
P.S. Beautiful photo of you with your daughter.
Cindy I loved this! That Boden dress is lovely. Love the sea green Mersea number too. You find the most unique pieces always. Nothing bland ever! Love how you style all of it. I am popping over to check more of those and the Texas dresses! I love you in the Frank & Eileen always. xo
Hi Kim
Thanks! The mersea caftan is such a beautiful color!
Hi Cindy
I don’t often comment but you and your daughter look absolutely perfect in that wedding photo!
Thank you Teresa
Hi,
Where is the white eyelet dress from?
I tried loft but could not find it.
Thanks,
K
Hi KD
If you click on the photo in the widget it will take you there. If that is the dress you are speaking of. All of the dresses in the photos are linked below the pictures.
I do love your posts Cindy and often find wonderful inspiration and ideas.
Just one thing, and I hesitate to mention it, your posts would benefit from a quick spell check and a proofread. I do not expect perfection in what is a friendly, chatty post. We all make mistakes and none of us are perfect. But this time the gremlins had really got to work and I found the mistakes were distracting from the content, which is a great pity.
Hi Patricia
Thank you so much for bringing that to my attention. Sometimes when I finish a post late at night and hit save. I will wake up the next morning to the same mistakes. That is what I get for working too late!
Thank you for being so gracious Cindy! Love your style x
Of course thank you!! I was busy getting ready for our kids and didn’t even look at it yikes!!
I love a maxi dress during the warmer days. I usually put one on after my errands or gardening the. A quick shower and an easy dress. One & done! It feels cool, elegant and so feminine. Funny coming from a jeans girl.
I do wear sleeveless even though my arms are not toned. I didn’t for a couple of years then thought this is silly. We all grow older. Wear the dress and feel cool on a hot day.
I love your Sezane dress!
Hi Joanna
Absolutely wear sleeveless. I rarely do, but applaud those who can and do!!
I LOVE a maxi dress and wear them all the time as they are so easy here in Florida…almost like the “house dresses” my mom used to wear. So many good options here, Cindy.
Mary Ann
You always look great in maxis and you are a petite!! House dresses …you are bringing back old memories!!
I’m a Soft Dramatic in the Kibbe system so I avoid dresses with lots of fabric. I’m a fan of wrap dresses, especially. But I found a great trick for shapeless linen shifts (ubiquitous for summer) that works for me! The dress “hack” is around the 2:00 mark. https://youtu.be/Mrc9YMtCUGw
I also use these at the back of dresses: https://m.media-amazon.com/images/I/71I2AiDlMiL._AC_UY695_.jpg
Love your blog! Stay cool in Paso!
Hi Valetta
That is a great hack!! Thanks for sharing!
I am 5’1” on a good day, and small boned. So many dresses these days overwhelm me, but I love the looks on women who can wear them. And I love dresses especially in warmer weather. I have found that caftan styles, which tend to have less volume, tend ton work better for me. I will wear mid-calf but midis are often like maxis on me. The one thing I don’t like about longer hemlines, is that when you sit down in a chair you have to be careful that the hem doesn’t droop to the ground.
At least I enjoyed looking at your selections! Loved at least 3 of them!
Hi Sheila
I totally understand. I have always had a hard time with dresses. The fabric can overwhelm me, and I am long-waisted!
Cindy!! How did you know I’m on the hunt for a new summer dress? Or two. So many choices. Wish there was an easy button but your suggestions have helped some. Just wish there were more in store shopping options. Order. Wait. Try on. Return. It’s driving me crazy!!! Thanks for tackling this subject. Dress weather is here! 👗
Hi Leslie
I hear you!! I had ordered a few for this post and they came last night at 7:00 too late. I will share the winners on Sunday!.
Good morning,
I absolutely love this post (as always!) and perfect timing too. I already live in dresses because of the soon-to-be here very humid NJ summers, along with my husband now taking a new job in Texas, so I appreciate all these suggestions! Do you have a link to the dress your daughter is wearing please? So pretty!
Hi Ann
Jenna bought the dress at the Sundance outlet last year. I linked two of them below the photo that I found on Poshmark. Here are the links:
https://go.shopmy.us/p-18459420
https://go.shopmy.us/p-18459956
Too much fabric on some of these for moi…while I love a dress for a put together outfit and for how cool they can be I do not want the longest length. How do you care for some of these? Have a good holiday
Hi KW
I totally understand. I don’t dryclean anything except wool pants, blazers or skirts. I wash everything in cold and hang to dry. I don’t iron my linen. I either lay it flat and yank it into shape or hang them up on a breezy day.