Stretchy, Comfy Summer Dresses for Midlife Women Under $50

The older I get, the more I care about comfort. I don’t want to wear anything scratchy, stiff, or tight. So, lately I’ve been leaning towards soft, stretchy summer dresses.

Today, I’m sharing seven summer dresses I found on Amazon that are cute, inexpensive, and so comfy you’ll never want to take them off.  

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1. Surplice Maxi feels like P.J.’s.

All the dresses I’m sharing, including this hot pink surplice maxi, have one thing in common: they feel like super comfy PJs or yoga pants! That’s because they’re made from light, smooth fabrics like rayon stretch jerseys.

They’re summery, super soft, and flowy – more like elevated loungewear with that relaxed, informal look and feel that everybody is after. And they’re feminine!  

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2. Comfy Drawstring Waist T-Shirt Dress

This comfy T-shirt dress is a bestseller on Amazon, and it’s no wonder. It’s light and ultra-soft, with a stretchy drawstring waistband that gives it a great shape but isn’t tight like a belt.

It’s also a handy dress to have in your closet when you feel a bit bloated. You can loosen or tighten the drawstring as you please, like a pair of joggers, and it always looks great.

This cute t-shirt dress comes in dozens of colors and prints. The length is perfect for gals our age – not too short, but not long and dowdy either!  

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3. Soft, Sleeveless Woven Shirtdress

This cheery red shirtdress from Amazon Essentials is a cute way to dress casually and feel comfy in summer. It’s 100% rayon, so it’s smooth and soft and has a comfy stretchy waistband under the self-belt.

I love the style. So many shirt dresses have a straight up and down cut, but this one has a fit and flare silhouette that nips in and gives you a more feminine shape.

Slip your hands in the pockets and do a little swing. This comfy, flirty sundress is great for every day.    

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5. Easy Cotton Polo Dress

Polo-style dresses, long and short, made for active lifestyles, can be super comfy.  This easy-wearing cotton dress is from one of my favorite brands on Amazon – Nautica.

I love the sporty sailor stripes, classy color block trim, and cute side slits. No buttons or zippers make this an extra comfy summer dress. Just pull it over your head and go!

And don’t you love that fresh, modern blue? It is a perky color and a modern change from the traditional navy or black striped dress.  

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6. Relaxed Empire Waist Maxi Dress

This pretty blue floral maxi dress is a comfy summer find. I love the perfect round neckline and high empire waist, which draws the eye upwards and lets your stomach breathe.

It’s a great way to camouflage a jelly belly.  Add a wicker bag, a pair of chic sunglasses, a touch of jewelry, and some classy sandals, and you’ll look fabulous! A few accessories go a long way.    

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7. Soft Tie Waist Sundress

I was thinking about tying on one this summer! Then check out this cute and comfortable Tie tie-waist sundress.

If you like short sundresses, this is great because of its soft feel and elegant, minimalist style.

The main focus is this soft, stretchy wrap waist belt. It’s built into the dress from behind and ties up at the front, creating curves where you didn’t know you had them!

This deep, rich wine color is gorgeous, but you can get this dress in many other pretty colors and prints.

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8. Stretchy T-Shirt Maxi Dress

No summer wardrobe would be complete without a stretchy,  sporty striped maxi dress.  Black and white are chic, and stripes are perfect for a nautical summer vibe.

When stripes are too thin or thick, they can often throw your proportions off, but with this dress, you will have no problem.  This fabulous maxi would be great for a poolside BBQ, beach, or cruise!  

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9. Short Stretchy Surplice Dress

If this looks familiar, it’s because it is the same dress as #1, except it is short.

I bought this dress again at a different length because I love the flattering neckline. It’s also so comfy and practical—you can swear it is a swimsuit coverup.

Easy, breezy, and soft, these cute coral dresses come in many colors and a few prints.

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9. Stretchy Tank Dress

This pretty floral dress is a variation on some of the other Amazon dresses I’ve been showing you, but this time with a tank-style neckline. It has plenty of stretch, so it feels good and gives you a great shape. The best part is that the straps are wide enough that you can wear a 

regular bra.  It comes in several colors and prints, so check it out.

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10. T-Shirt Maxi

This thin, light T-shirt maxi dress is silky, super soft, and flowy—perfect for my gals who love anything bodycon. Me—I wear shapewear with this one!

  Amazon has many more super comfy casual summer maxi dresses in many colors and styles. Many are from Amazon Essentials, their brand of wardrobe basics, so be sure to check them out!