Amazon’s Most Flattering Dresses for Women Over 50 This Summer

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I think wearing dresses in the summer is UNDER-rated. They are cool, chic, and you don’t have to overthink your outfit. Not to mention, it’s pretty easy to take dresses from day to night just by changing your accessories. If you’ve been thinking it’s time to freshen up your closet with some easy-breezy summer dresses, I’ve got you covered. Plus, they’re affordable! I’ve rounded up Amazon’s most flattering dresses for women over 50 this summer. And you know I’m always looking for dresses that are comfy, breathable, and don’t cling where we don’t want ’em to. Let’s get to the fun part!

What’s The Most Flattering Dress For Your Shape?

The most flattering dress for your body shape enhances your natural silhouette. If you have an hourglass shape, fitted styles like wrap dresses or belted sheath dresses highlight your balanced curves. For a pear-shaped body, A-line or fit-and-flare dresses draw attention upward and skim over hips. Apple-shaped figures often look best in empire waist or shift dresses that create definition just below the bust while floating over the midsection. If you’re rectangle-shaped, dresses with ruching, peplums, or cinched waists create curves and add dimension. For inverted triangle shapes, look for dresses with fuller skirts or details at the hips to balance broader shoulders.

Amazon’s Most Flattering Dresses for Women Over 50 This Summer

Flutter Sleeve Smocked Midi Dress

Tania Stephens wearing a blue flutter sleeve smocked midi dress with clear wedge sandals and gold hoop earrings, perfect for summer events.
Flutter Sleeve Smocked Midi DressBaby Knot Earrings (Use code STEPHENS15 for 15% off) | Clear Strap Wedge Shoes (Size 9.5)

This Flutter Sleeve Midi Dress might be my favorite of the bunch. The flutter sleeves are sweet without being too frilly, and they’re perfect for giving the upper arm a little coverage. The smocked bodice is wonderfully forgiving and flattering, it hugs in the right places without feeling tight. I love the soft tiers that give this dress some movement, and yes, it has pockets! I wore mine with Clear Strap Wedges for an easy dressed-up look, but it would be just as cute with flats for a casual lunch with friends.

Floral Boho Maxi Dress

Tania Stephens styled in a floral boho maxi dress layered with a white scrunched-sleeve blazer, accessorized with hoop earrings and woven pearl heels.
Scuba Knit Stretch Blazer with Scrunch Sleeves (Medium) | Floral Boho Maxi Dress (Medium) | Large Hoop Earrings | Woven pearl heeled sandals (TTS)

Sometimes you want to be floaty and feminine, and other times you want to toss a blazer over it and feel a little more polished. This Boho Maxi Dress works for both moods. The floral print is cheerful but not over the top, and the fabric has that light, breezy feel that’s perfect for warmer days. I paired it with a scrunched-sleeve blazer for a fun high-low mix that could go from church to dinner without missing a beat. Add sandals or heels depending on how fancy you’re feeling.

Smocked Waist Midi Dress

Tania Stephens in a navy long-sleeve V-neck smocked waist midi dress with pointed-toe bow slingbacks and a tan faux leather shoulder bag.
Long Sleeve V Neck Smocked Waist Dress (Medium) | Bow Pointed-Toe Slingback Flats (TTS) | Faux Leather Shoulder Bag

This Long Sleeve Dress is the kind of dress you’ll reach for over and over again. It’s got a soft, smocked waist that defines the figure gently (no pinching!), a flattering V-neckline, and sleeves that hit just the right length. The material feels light but not flimsy, and it moves beautifully when you walk. I styled it with a Faux Leather Shoulder Bag and my favorite bow Slingback Flats, and it felt just right for everything from a baby shower to Sunday brunch.

Summer Maxi T-Shirt Dress

Short Sleeve Crewneck Tie Waist Dress (Medium) | Large Hoop Earrings | Large Cross 14k Pendant Necklace | 14k Small Mantra Necklace (Use code TANIA15, for 15% off) | Navy Suede Pumps (TTS) | Dumpling Cloud Bag

This Tie Waist Dress is like your favorite t-shirt, but make it fashionable. I love the tie waist! It creates shape without feeling too snug, and that side slit makes it easy to move around (or chase grandkids, lol). The fabric is soft and feels breathable, always a win. Perfect for casual errands or wearing to dinner.

Summer Loose Boho Flowy Wrap V Neck Maxi Dress

This Boho Maxi Dress has a flattering wrap style and the slit gives it a little sass without being over the top. The floral print is feminine but not too bold, perfect for weddings or vacation dinners. I love the 3/4 sleeves for a bit of arm coverage, and the fabric is light and airy on hot days. Throw on a wedge and some bangles and you’re good to go!

Boho Maxi Dress V Neck Puff Sleeve

I’m a sucker for a puff sleeve, and this Boho Maxi Dress is doing it right. The swingy fit and flowy fabric make it ideal for hot summer days when you still want to look pulled together. Plus, the floral pattern comes in some beautiful colorways, so there’s one for every skin tone. Super comfy and it twirls like a dream, ha!

Spaghetti Strap Smocked Maxi Dress

This Spaghetti Strap Maxi Dress is for my Gurls who love a little romance in their wardrobe. The ruffles, the smocking, the floaty layers, it’s all working together to give major summer vibes. The straps are adjustable (praise hands!) and the length is long enough to wear with flat sandals. Great for beach dinners or casual brunches with the girls.

Short Sleeve T-Shirt Maxi Dress

Sometimes you just need a go-to, comfy T-Shirt Dress that still looks put together, and this one nails it. It’s a classic crewneck style with short sleeves and a long length that keeps you covered without overheating. It’s soft, stretchy, and comes in lots of colors, so you might just want more than one. Add a straw hat and cute tote, and you’ve got an outfit!

Criss Cross Halterneck Maxi Dress

How pretty is this?! This Maxi Dress has a fun halterneck with criss-cross detailing that’s super flattering on the shoulders. Seriously, we should show those off more. The A-line shape gives room to move while still looking polished, and that floral print is just the right balance of pretty and punchy. This one’s perfect if you’ve got a summer event coming up and want something that looks like you tried without trying too hard. It’s also lightweight, so you’ll stay cool and cute. Lots of other colors at the link.

Flutter Sleeve Smocked Midi Dress

You know I love a flutter sleeve! It covers the upper arm without feeling bulky and gives a nice detail to an otherwise simple dress. This midi-length dress is smocked in all the right places (hello waistline!) and has cute tiers that make it flowy and fun. The fabric is breathable, and the whole look is perfect for everything from Sunday lunch to shopping with your daughter. It even has pockets, y’all!

Cotton Short Sleeve Shirt Dress

This Short Sleeve Shirt Dress has that easy, coastal-grandma look that’s just timeless. It’s a button-down with short sleeves and pockets, so it’s cute and practical. I love the shirt-dress silhouette; it looks great with white sneakers or strappy sandals. Toss on a belt or leave it loose depending on your mood.

Casual Button Down Shirt Dress

Here’s another comfy favorite with a relaxed fit and that effortless summer style. The button details on this Shirt Dress add just enough polish, and the sleeves are short without being too tight. You can wear it open as a beach cover-up or buttoned up for running errands. It’s easy-breezy and looks adorable with a crossbody bag.


That’s it, Gurls, Amazon’s most flattering dresses for women over 50 this summer. Grab your favorites now before your size disappears or your favorite color is no longer available!

Let me know which one’s your favorite when you try them!

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126 Comments

  1. 🙂 I am not a big maxi fan, they swallow me up but I do like a shorter more form fitting dress.

  2. Catherine says:

    🙂 loved all the dresses you showed. Oh the decisions we have.

  3. Angela C. Dixon says:

    🙂 Thank you for all you do.

  4. 😊Love the maxi dresses, especially the lime green Boho.

  5. Laura Terry says:

    Found it! I love many of the dresses you’ve styled but especially like the criss-cross maxi dress. It’s in my cart right now. I love your blog and read it daily.

  6. Donna Huberty says:

    🙂 The criss cross halter dress is so cute!

  7. Susan Lindsay says:

    😊 such pretty dresses!

  8. 😊 I love a flutter sleeve too!

  9. 😊 I love dresses and skirts in the summer; easy, cool and comfy!

  10. Cynthia C. says:

    🙂 Found it! Fabulous dresses! So many to choose from!

  11. 🙂 The navy and white spaghetti strap dress is very pretty. Hope you and Joe are having a good time.

  12. The Tee-shirt short sleeve tie waist dress in navy is my favorite 🙂

  13. 🙂 I really like the side ruched navy dress. I’m not much of a dress person. But I do have a nice red, white and blue printed dress I plan on wearing on the 4th of July. I bought it years ago from a Dress Barn before they all closed. I finally lost a few pounds where I can finally wear it.

  14. nancy norcross says:

    🙂 I love dresses in the summer.

  15. Love the dresses. We’re you eating somewhere at Calabash?

    1. It was Joe’s Bar & Grill.

  16. Ruth Shave says:

    🙂 Love the waist on the t-shirt maxi dress. It hides so much!

  17. 😊 Cute dresses especially the blue ones you’re wearing.

  18. 😊 spaghetti strap dress is sooo summer. Cute

  19. 🙂 great choices of dresses. I really like the green one with the white stretch blazer.
    I checked thr blazer but I am petite and the length is over 26″. Bummer!!!!

  20. 😁 I love dresses for summer and the blue shirt dress is my favorite!

  21. Stephanie Weeks says:

    I love wearing dresses in the summer time. 😊

  22. 🙂 I noticed mid length hemlines are very popular now. I used to think only for old ladies but have changed my mind

  23. Darlene Bright says:

    😊 I love several of these dresses!

  24. Kathy Taylor says:

    Really love the blue dress.. Found It. 🤓😎😊

  25. Cute dresses! My favorite is the navy dress that ties at the waist. 🙂

  26. 🙂 Verse of the Day was perfect for me today. Thank you for always including this.

  27. Karen Gunter says:

    Dresses are great for the summer. I especially like the eyelet one. 🙂

  28. Karen Gunter says:

    I love dresses in the summer. I especially like the eyelet one. 🙂

  29. Love the light blue eyelet dress. It looks so good on you!

  30. Carolyn (petite) says:

    All the dresses you modeled look amazing on you! 🙂 The eyelet one is stunning!

  31. Danette Enzminger says:

    😊 some cute dresses.

    1. Margie Gleeson says:

      😊 I, also like your first one best

    2. Margie Gleeson says:

      😊 I like especially like the lime green dress

  32. 🙂 beautiful dresses.

  33. Great ideas! 😊 Found it! So cleverly hidden!

  34. I like the crisscross halterneck dress and the smocked dress too.
    The Blue laced dress looks good on you with blonde hair/ blue eyes!

  35. 😀. Love the shirt dresses. So cute and casual!

  36. 🙂 I have a new love for midi dresses! So comfy and flattering.

  37. Gayle Davis says:

    🙂. I have embraced dresses this spring! So much cooler than pants.

  38. 😊I like that you included a cotton option. I’m pay more attention to fabrics lately.

  39. 😊 The boho maxi is my favorite!

  40. Ginger Hiller says:

    😃 How nice of the raccoon to entertain you during your dinner. 😉 The only time I don’t like wearing a dress during the summer is when it’s raining and I have to use an umbrella. I just ordered the bright pink short sleeve tshirt dress. I hope that y’all are having nice weather.

  41. Jenniffer Groski says:

    😁I love the green boho dress but I’m too short for the length. I really like the shirt dresses!!!

  42. Elizabeth Tobin says:

    😊I love the eyelet dress! I need to add more dresses to my closet!

  43. ☺️So many pretty dresses! And one of my favorite verses.

  44. 🙂 ALL the dresses are great! My favorite is the blue smocked flutter, eyelet, followed by the navy and white spaghetti strap. Raccoons! oh my! We are trying to get rid of them!

  45. Beautiful dresses. Are you in Calabash, NC? Maybe on the Intercoastal Waterway in NMB?

    1. No, we were at Joe’s Bar & Grill in North Myrtle Beach.

  46. Beverly Hawkins says:

    😊 Great choices
    Enjoy your time together

  47. 🙂 I love wearing dresses in the summer. Easy breezy and comfortable.
    A view with dinner lovely!

  48. 🙂 I like the flutter sleeve smoked midi.

  49. 😊 Love the first dress ( have it in navy)….

  50. Sonja Allen says:

    🙂 Pretty Pretty Pretty

  51. sue koren says:

    🙂 Love the eyelet dress

  52. sue koren says:

    🙂 Love the eyelet dress

  53. Found it 😀
    Love you in the lime green with white jacket!💚
    Were you at Greg Norman’s Steakhouse?

    1. We were at Joe’s Bar & Grill in North Myrtle Beach.

  54. 🙂
    Absolutely LOVE that Boho dress!

  55. 😊 Some cute dresses here. The light blue flutter sleeve one looks nice on you. I don’t like raccoons anymore. Two or three years ago we had a nest of baby robins in a tree in front of our house and a raccoon climbed up there during the night and got them. We know it was a raccoon because we saw it on video. They are cute critters but that’s about it.

  56. 😊 Found it! Love the flutter sleeve dress and the navy dress, both look very pretty on you.

  57. Roberta Schwandner says:

    😃Cute dresses.

  58. 🙂 have not had much luck with Amazon dresses. They are usually too long on me and most don’t come in petite lengths

  59. 🙂 found it! I am loving dresses this summer, one and done outfits. I have the green and white smocked sundress, and will try a white blazer with it, per your suggestion/outfit. Have a blessed week!

  60. 🙂 great options for all body types. I especially like the blue eyelet dress

  61. 🙂 Good options here. I always chuckle when I’m wearing something you mention in your post. Today’s outfit is a comfy t-shirt type dress.

  62. Sue Debord says:

    😀 cute dresses.

  63. Sara Beck says:

    Found it :). The dresses are all really cute

  64. Julie Wood says:

    😊 I bought the tie waist dress and I love it! I think people dress so casually anymore that when they see someone in a dress it is shocking. I love dresses and I agree, it takes the thought out of what top and what bottom goes together. Out the door you can go with a dress!

    Yesterday I posted the word illuminate instead of eliminate and I could not go back and change it. Haha! I was afraid the grammar police would get me!!!

  65. Good timing as I need a dress for family pictures!
    Found it!!

  66. 😀 I agree dresses are SO easy!!! I like the smocked maxi

  67. FOUND IT
    Love the eyelet blue and navy dress – but all of them are great dresses
    I love dresses too

  68. 😀 That green maxi sundress! Every time I see it, so cute on you! I really like the button dress, pretty color.

  69. 😊 so many cute dresses. Love the puff sleeved dress.

  70. Mary Beth says:

    😊 Thanks for showing something for every body type. My favorite is the cotton short sleeve shirt dress. It’s so versatile, it could go from beach coverup to casual dinner date.

  71. 😊 Whenever I wear a dress my husband ask what’s the occasion.

  72. 🙂 Cute dresses!! I have a hard time figuring out my body shape! LOL

  73. Deborah M says:

    Looks like you were dining at Joe’s Bar and Grill. Have been there many times while on vacation. The food is fabulous and the service is impeccable! Love all the adorable dresses. Wish they were available in petite sizes.

  74. I live in dresses in the summer…so easy! You have featured some great choices! Happy Wednesday❤❤❤

  75. Found it!
    My favorite is the green and white boho dress and all of the accessories shown. The sandal heels are so pretty.

  76. ☺️ beautiful dresses

  77. Tania, where You&Joe had dinner, would it be Joe’s Bar&Grill? Also, did you get my email I sent you on Monday? Hope you’re enjoying your time here!

    1. That’s where we were. I appreciate the recommendation.

  78. 🙂 Dresses are so comfortable!

  79. Jeannie W says:

    😊Love the blue tie waist dress.

  80. I have the blue flutter sleeve midi dress! I might wear it for family pictures this weekend! 😊

  81. Found it 🙂 Love the Amazon smocked dress.

  82. 🙂 love the white blazer

  83. 😊 The flutter sleeve smock midi is so cute!!

  84. 🙂 I love a summer dress and the beautiful blue crew neck tie waist is on sale.

  85. Susan E Cantwell1 says:

    😊 So many pretty dresses! Hard to choose just one! 😊

  86. Wendy Lightfoot says:

    🙂 The sling back flats are a fun look

  87. Wendy Lightfoot says:

    🙂 The slingback flats are a fun look

  88. Phyllis p says:

    🙂 lots of choices

  89. Popped in to say I have the last dress featured, casual button down shirt dress. I purchased the dress in navy and absolutely love it! It washes well, I hang to dry. It can easily be dressed up or down!

  90. ☺️love the green and white dress and that navy is stunning on you!

  91. 🙂 Found it! Clever placement! So many cute dresses! Thanks for guidance with body types!

  92. Traci Woody says:

    🙂 I like the length of this dress, and you wear the color very well!

  93. Cynthia Fisher says:

    Found it.

    LOVE wearing dresses in the summer. It’s so easy!!

  94. Gail Medeiros says:

    😊The casual button down dress is my favorite. Thanks for all the great ideas.

  95. Priscilla Patterson says:

    You were eating at Joe’s in Myrtle Beach. Love watching the raccoon family there!
    Love the green and white maxi!

    1. Yes, that’s where we were eating!

  96. 😊
    The flutter sleeve and short sleeve shirt dress are my picks.

  97. I enjoy dresses as well. Tshirt dresses and the light denim dresses are comfy and cool in the summer. Plus, there’s no bulk around the tummy. Wishing you lots of blessings today.
    Found it. 😊

  98. Charlie Watt says:

    😊. The blue eyelet is my favorite.

  99. 🙂 I love the tie waist dress!

  100. Jan Canapp says:

    😀
    Can’t go wrong with a shirt dress in the summer. I’m loving both of them.

  101. Thank you for all the great dress ideas.
    🙂

  102. 😀 no I don’t know where you are eating and great information for different shapes for dresses!

  103. 😊I liked all the dresses.

  104. Carol Ann Jablonski says:

    🙂 The flutter sleeve midi dress is so pretty on you. I can see why you consider it a favorite.

  105. Joe’s Bar and Grill! Love it; I also like Hamburger Joes for a casual meal! Their onion rings can’t be beat!

    Love the dresses for 50 plus!

  106. 😊
    Love the navy t-shirt dress. Very flattering.

  107. Kathleen S says:

    😀I cannot pick a fav, they are all lovely!

  108. 😊I love wearing dresses in the summer

  109. 😀perfect scripture verse for me today. I have the light blue smocked waist dress in the short version & love it! Sounded like you had a great supper! 🦝🎣

  110. I like the Boho look.
    Found it 🙂

  111. Kathy Laweryson says:

    found it!

    I’m really liking the tiered dresses, especially with the flutter sleeves.

  112. This week I have not found the 😀 but I’ll keep trying