Best Summer Maxi Dresses for Women Over 50 That Are Flattering

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Where are my dress-loving Gurls? My sister recently moved back to Tennessee, and she and her family finally got settled enough to try a new church. She is used to going to church in Atlanta, where everything goes, jeans, dresses, shorts. It’s not like that in our small town; most all of the women were in dresses. My sister loves the church, but she complained that now she’ll have to update her wardrobe. Ha! Lucky for her, today I’m sharing the best summer maxi dresses for women over 50. All perfect for church and other events!

Best Summer Maxi Dresses for Women Over 50

A Splash of Sunshine and Sky

Woman wearing a colorful blue and green floral maxi dress with a light blue cardigan – best summer maxi dresses for women over 50
Spaghetti Strap Square Neck Casual Maxi Dress (Large) | Similar Open Front Cardigan Sweater (Medium) | Clear Two Strap Wedge ( Sized Up – 9.5) | Quilted Crossbody Bag

This boldly printed Maxi Dress is an instant mood-lifter with its vibrant mix of lime, aqua, and cobalt. The smocked bodice gives a comfortable fit that moves with you, and the flowy tiers keep it light and airy for hot summer days. I added a pale blue cardigan for a soft layer that tones things down just a bit. A neutral block heel and creamy shoulder bag finish the outfit in a way that feels pulled together but still relaxed. Perfect for vacation dinners or weekend outings close to home.

Style tip: If bright prints make you nervous, add a solid layer like this soft cardigan to ground the look and give your eyes a place to rest.

Delicate Florals with Feminine Flair

Pink and green floral maxi dress with blush blazer for summer garden party
One Shoulder Sleeveless Maxi Dress (Large) | Pink  3/4 Sleeve Blazer (Large) | Reef Wedge Slingback Sandal (Size 9 – needed a 9.5) | Quilted Crossbody Bag 

Soft green and blush pink are a timeless pairing, and this pretty Maxi Dress brings the two together in a way that feels fresh and elegant. The small floral print is sweet but not too youthful, and the pink knit blazer adds polish without feeling fussy. I wore this look to lunch with friends, and I can see it working for garden parties or casual weddings, too.

Style tip: Try layering a structured knit blazer over flowy dresses for a flattering shape that still feels easy to wear.

Chic in Green and Ivory

Green smocked maxi dress with white blazer – flattering maxi dresses for mature women
Scuba Knit Stretch Blazer with Scrunch Sleeves (Medium) | Floral Boho Maxi Dress (Medium) | Large Hoop Earrings | Woven pearl heeled sandals (TTS)

This vibrant green Maxi Dress with white print feels like summer in a dress. The smocked top offers a forgiving and flattering fit, and the full skirt is breezy without overwhelming. I paired it with a winter white Knit Stretch Blazer to dress it up a bit, making it a wonderful option for a more elevated occasion. A pair of pearl heeled sandals and some gold jewelry brought the whole look together without competing with the bold pattern.

Style tip: Smocking is your friend when you’re between sizes. It gives you some wiggle room while still creating shape.

Soft Pink with a Denim Twist

Casual pink maxi dress styled with denim jacket and brown crossbody
Pink Tank Sundress (Large) | Stretch Denim Jacket (Large) | Similar Chunky Necklace | Large Hoop Earrings | Large Cross 14k Pendant Necklace | 14k Small Mantra Necklace (Use code TANIA15, for 15% off) | Vionic Ankle Straps Heeled Sandal (TTS) | Woven Crossbody

This soft pink maxi is simplicity at its best. The color is cheerful without being too bright, and the cut is easy to wear for just about any body type. I layered on my favorite Stretch Denim Jacket and added a Woven Crossbody for a laid-back, everyday vibe. This is the kind of outfit I reach for when I want to feel pretty but comfortable, running errands, heading to church, or grabbing a coffee.

Style tip: A denim jacket is the ultimate outfit finisher. It brings structure to softer dresses and helps balance the look.

Soft Green with a Hint of Boho

Soft green boho-inspired floral maxi with white crochet cardigan and neutral heels
Smocked Maxi Dress (Medium) | Pointelle Open Cardigan (Medium) | Convertible Shoulder Crossbody Bag | Draper James Cat Eye Sunglasses | Wedge Dress Sandals

This green floral Maxi Dress has a breezy, boho-inspired feel that I absolutely love for summer. The print is soft and subtle, and the tiered skirt gives it movement that’s fun to wear. I added a crochet cardigan for a bit of texture and warmth, and kept the accessories neutral and natural-looking. This is an easy choice for weekend brunch, outdoor concerts, or strolling the farmer’s market.

Style tip: When wearing midis or maxis with open-toe shoes, choose a heel with a bit of lift to elongate the legs just a touch.

Effortless Jersey Maxi Dress – Pretty Medallion

This Maxi Dress had me at effortless. The medallion print is so flattering, and the jersey fabric moves with you, not against you, which is great if you’re wrangling grandkids. The A-line skirt gives a nice flow, and the empire waist? Chef’s kiss. I’d pair it with strappy sandals and a denim jacket for a polished but comfy look.

Side-Tie Maxi Dress – Floral Paisley

Talk about pretty! This floral Maxi Dress has a little side tie detail that makes the waist look cinched, even if you just had a second helping of peach cobbler. The rayon fabric keeps it breathable, and I love the pink and white palette for summer events. Wear it to church, brunch, or your neighbor’s birthday bash. Bonus: the side slits make walking easy and stylish.

Sleeveless Jersey Maxi Dress

This Maxi Dress is your “throw on and go” dress, and we all need one of those in our summer wardrobe. It’s sleeveless, comfy, and has a nice clean line that works on lots of body types, even if your bust and waist are not quite where they used to be. ha! Pair it with sneakers for errands or dress it up with a long necklace and your favorite heels. Throw on a light cardigan if you don’t want your arms to show.

Print Long Sleeve Ruffle Hem Maxi Dress

This Maxi Dress is giving special occasion dress in the best way. The ruffled hem adds a little drama (but not too much, we’re not in our Real Housewives era, ha!). The sleeves are perfect if you’re not into showing arms, and the fabric has a silky drape that feels luxurious. Add simple jewelry and sandals for an elegant evening vibe, or style it down with flats and a tote bag for day wear.

Old Navy Sleeveless Fit & Flare Maxi Dress

Gurls, this is your everyday wear kind of Maxi Dress. Lightweight, breathable, and just enough flare in the skirt to feel swishy. The floral print is casual enough for a lot of events, but if you want to go fancy, check out the navy version.

Old Navy Puff-Sleeve Smocked-Bodice Maxi Dress

You know I’m a sucker for flutter sleeves! Okay, this Maxi Dress might be a bit MUCH for church, lol. I love the keyhole bodice and the fact that it comes in a ton of great colors. This would be great for a party or evening wedding. Heck, you do you. Throw on some sandals and go be the best-dressed one at Target. lol

Amazon Short Sleeve Maxi Dress

Let’s talk comfort, this Maxi Dress is made for real life. Short sleeves, a flattering shape that hides all the things, and machine washable. It comes in a bunch of colors, so pick your mood: florals, solids, stripes…you name it. You could dress this up with wedge sandals and a little jewelry, or just wear it with flip-flops to walk the dog.

Amazon Square Neck Maxi Dress

If you’re into a little flair, this Maxi Dress brings it! It feels fancy but isn’t fussy; the cotton blend fabric breathes beautifully on hot days. I don’t think the square neckline gets enough love. It’s so flattering! I’d wear this to a summer date night or throw on a light sweater for church. Pair it with statement earrings and a wooden clutch for extra elegance.

J.Jill Popover Shirtdress

This one’s for the Gurls who love a Shirtdress vibe. It’s breezy, has sleeves, and gives that effortless “I woke up like this” polish. I love the soft structure, not too clingy, not too boxy. Belt it to show off the waist or leave it loose and flowy. Great with sandals and sunglasses on a casual summer day.

Whew! There you have it, the Best Summer Maxi Dresses for Women Over 50! Whether you’re into florals, pockets, or flutter sleeves, there’s something here that’ll fit your mood and your silhouette. Just remember: no matter what size you are, you deserve to feel beautiful in your clothes.

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weeping may stay for the night,
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84 Comments

  1. Lynn glenn says:

    I read your blogs every day!! sometimes one slips by, but I catch up on it!!
    Love them.

  2. 🙂 The green and pink is my favorite, all great items!

  3. Donna Basile says:

    😃Found it! The flower arrangement is absolutely beautiful!! Nothing beats fresh flowers & Farmers markets🥰🥰

  4. 😊I like the Effortless Maxi

  5. One of my favorite blogs— I loved every dress but especially the Boho!! It was so pretty 🌼

  6. Elizabeth Tobin says:

    😊Lots of pretty choices. Finding a flattering maxi can be a challenge for me as I’m petite. The Talbots styles that are more fitted tend to look better on me.

  7. Found it🙂. So many great dresses!

  8. Julie Herr says:

    🙂. Beautiful dresses! I wish they came in petite!

  9. Deborah M says:

    😊. I love maxi dresses. Thank you for the styling tips… things I wouldn’t think of.

  10. 😊 Beautiful dresses! The first one was my favorite. I love the colors!

  11. Danette Enzminger says:

    😊 some great options.

  12. 😊Cute dresses. Maxi’s and longer midi’s are the only dresses I now wear.

  13. 😊 This really seems to be the summer of the dress! I shopped for midi length floral dresses with short to elbow length sleeves in my area last week and came up lacking – maybe I’m asking too much?

  14. Stephanie Weeks says:

    Perfect time of year for these kind of dresses.

  15. 😄 Summer dresses are a great option to look put together and comfortable.

  16. Lots of cute dresses! 🙂 found it!

  17. 😊some great options!

  18. Ginger Hiller says:

    😃 Fabulous scripture today! Since I love wearing maxi dresses during the hot months, I am going to checkout three that you shared, the blue medallion, the side tie, and the soft pink one.

  19. FOUND IT!
    Great dresses

  20. ☺️
    The soft pink dress with denim is perfect.

  21. 😊 love dresses in the summer

  22. 🙂 I Love the first dress so pretty. Lots of beautiful options. Have a great weekend.

  23. I found it. 😀😀😀

  24. Kathy Laweryson says:

    found it!

    those green dresses look so pretty on you! I like that pink floral square neck dress.

  25. Cynthia C. says:

    🙂 Found it!! Love the pinkish ruffle hem from Nordstrom!!

  26. 😀. Love the popover shirt dress. So pretty!

  27. 🙂 The first dress is hands down my fave. The colors are so lovely! And I like the sweaters and jackets for those sleeveless dresses. I’m cold at work, church, restaurants, movies…

  28. 😊 Cute dresses! I really like the pink tank dress.

  29. 🙂 The vibrant green with the white jacket is my favorite.

  30. Stella Gustafson says:

    😀 Found it

  31. Stella Gustafson says:

    Love the maxi dress with the vibrant mix of lime, aqua, and cobalt may just have to put it in my cart

  32. ☺️ I love the way you style sundresses so that they are appropriate for church!

  33. Brenda S. says:

    I love wearing Maxie dresses in the summer. I feel cooler in them than shorts.🙂

  34. 🙂
    Really like that jjill popover and the pretty first pattern one.

  35. Karen Gunter says:

    🙂
    midi and maxi dresses are my favorites for summer. Thanks for the great selections

  36. Linda Fleming says:

    I love the Maxi dresses but wish you would include some for those of us who are vertically challenged 🥰

  37. Leslie Daulton says:

    love the effortless jersey maxi and it comes in petite. Amazon dresses do not so would have to hem them. so many of them are tiered now days which makes it difficult without looking weird.

  38. 🙂 Nice dresses. Don’t know where the Friday the 13th superstition started.

  39. 😊 You show some really pretty maxi dresses here. I tend to stay away from that length though, I’m 5’ 4” and feel like I look frumpy in them.

  40. 😀beautiful dresses!

  41. 😊 Cute dresses. Sweaters are appropriate in many churches because air conditioning keeps them chilly! So, showing sundresses with cute coordinating tops is perfect!

  42. Judy Mumford says:

    I don’t understand how you look so pretty and fashionable in long dresses. I’m 5’4 , 140 and when I try anything mid calf or longer I look short and fat. Any tips for me to try?

    1. I’m sure you are being too hard on yourself. An easy way to look taller in long dresses is to wear wedge heels. They are more comfortable and easier to walk in than most heels. Also, look for dresses with an empire or high waist. The higher the waistline hits, the longer your legs will look.

  43. 😊Love the floral paisley

  44. 😀 Both those green and white dresses are for me, love them.

  45. 😀 love the print & color palette of the 1st maxi!!!

  46. So many beautiful options! I appreciate the different price points! I’m sure you’re happy to have your sister close by…Happy Friday❤❤❤

  47. sue koren says:

    🙂 These are all such pretty options!

  48. Donna Huberty says:

    🙂 The jersey maxi dress is very pretty!

  49. Angela C. Dixon says:

    🙂 I love the green, turquois dress!
    Thank you for doing what you do!

  50. Mary-Ellen Mckay says:

    Found it 😊. Did you know that “Triskaidekaphobia” – is the fear of the number 13 ! In the bible, the night before Jesus’ arrest, he invites his 12 apostles to dine with him. Including Jesus, this is a party of 13. Because Jesus died shortly after the Last Supper, the number 13 is now considered unlucky. The Last Supper may be the origin of triskaidekaphobia.

  51. 😃 The green and white maxi has been in my Amazon cart since the first time you featured it. I love it, I just don’t see myself wearing it. So many pretty dresses!

  52. Teri O’Brien says:

    😀such cute dresses

  53. Sue Debord says:

    Cute dresses. 😀

  54. Love the square neck (and so many different fabrics!) and the shirt dress. I love wearing dresses!

  55. Love the green floral maxi dress! 🙂

  56. 🙂 I, too, wear dresses to church each Sunday and like to add a new maxi/midi each season. Thanks for sharing these options.

  57. Sonja Allen says:

    🙂 Wow! Lots of pretty dresses!!!

  58. Susan E Cantwell says:

    😊Cute dresses!

  59. 🙂 Dresses are so easy and comfortable in summer.

  60. Nancy Darden says:

    : ) Trying to wear more dresses.

  61. Cynthia Fisher says:

    🙂not much of a maxi wearer but these are cute

  62. Love the green maxi dress!

  63. 😁So many cute dresses I can’t pick a favorite

  64. Charlie Watt says:

    😊. Love the delicate floral with the pink jacket. Some of your photos look like they are taken at the Martha Washington!

  65. Carolyn (petite) says:

    All the dresses you modeled are so beautiful! I especially think floral maxi dresses are so lovely. Love the green floral one and the green and pink floral one. 🙂

  66. 😊 there is something that I love about the soft pink with the denim jacket. The green dress with the point Elle cardigan is another favorite.

  67. 🙂 Oh, how I love a summer maxi!

  68. Dorothy Kennedy says:

    🙂 The dresses are all so cute but I am partial to the tiny floral ones.

  69. 🙂 I like the style tip for wearing a heel when wearing midis or maxis.

  70. Beverly Hawkins says:

    😀 I love the ease of wearing a dress in summer.

  71. ☺️beautiful dresses!

  72. 🙂 I googled to double check why 13 is considered unlucky, it goes back to Judas being the 13th apostle, along with Norse mythology of Loki’s disruptive presence at god’s dinner. I have several maxi’s and need to wear them, even though at 5’3″ they feel like too much fabric. Have a blessed day!

    1. Joe had mentioned it was something like that.

  73. 😊 love these dresses especially the Vince Camuto red and pink one. I clicked on inspo outfit of the day for the adorable shell earrings, but didn’t see them in link. May I please have a link. They are adorable for upcoming beach vacation. 😎 Today is my son’s birthday and he was born on Friday the 13th, so always lucky for our family!

  74. 😀 my favorite is the vibrant green and white maxi dress. Very cute

  75. Kathleen S says:

    😀all very nice. I remember growing up, we got a new dress for Easter and Christmas, wore it to church every Sunday until the next one. Then it became a school dress if it fit. Now they do wear anything here.

  76. Sara Beck says:

    Found it 🙂 Love all the dresses.