Best Comfy, Summer Dresses Over 50

If you avoid wearing casual dresses in spring and summer because they feel stiff and uncomfortable, you need to see what I’ve found! Here are seven inexpensive, stretchy summer dresses that are easy, breezy, and so comfy that you’ll never want to take them off.

Dress | Sandals

1. Floral T-Shirt Dress

The next best thing to wearing a comfy t-shirt is a comfy t-shirt dress! This one is my favorite. It’s light, super soft, and has a stretchy drawstring waistband that gives you a nice shape but isn’t tight like a belt. This is a handy dress on those days when you are feeling a bit bloated. You can loosen or tighten the drawstring as you please, the same way you would a pair of joggers, and it always looks great.

I’m crazy about this sunny, yellow floral print, but there are dozens of other colors and prints. I think the length is great for gals our age – not too short, but not long and dowdy either!

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Dress | Sandals

3. Swingy Shirtdress

A shirtdress is a chic way to keep cool and look casual this summer. I’m getting a lot of wear out of this flared shirtdress in this gorgeous red and white print. This dress is very soft, with a stretchy waistband under the self-belt.

I love this idea because so many shirt dresses are straight up and down, but this nipped-in waist gives the dress a more feminine shape. Slip your hands in the pockets and do a little swing. This is a happy, fun sundress that is great for every day.

Dress| Sandals

4. Fit and Flare T-Shirt Dress

This pretty floral t-shirt dress is similar to the yellow floral one I showed you at the top of this post, except this is a fit and flare, while the other is column style. It comes in dozens of colors and prints, but vintage floral prints like this are trending, and the gorgeous pinky/blush is so fresh.

The cut is fabulous; streamlined up top, with a gentle flare at the waist. This dress is easy to dress up with a pair of strappy sandals and some pretty jewelry or keep it casual with a denim jacket and your favorite pair of flat sandals.

Dress| Sandals

5. Striped Shift Dress 

Ahoy! I always love a nautical touch in the summer, and this year it’s all about this modern Bretton stripe tunic. Bold colors are trending, and I love how they have taken this very traditional print and made it very 2022 with that bright blue! The white color block trim is modern and fabulous. In fact, who needs jewelry?  Pair this short sundress with flat slides. My favorite are these Raffi H-sandals, which are oh, so chic.

Dress| Sandals

6. Wrap Front Dressdress

Think about tying on one this summer! I’m talking about this dress. If you can handle a slightly shorter dress, this is a great one because of its elegant, minimalist style. The main detail is a beautiful wrap belt built into the dress from behind and ties at the front, giving you an excellent fit and curves where you didn’t know you had them! This wine color is deep and rich, but this dress comes in various styles and colors. Great for parties too.

Dress| Sandals

7. Striped Maxi Dress

Your summer wardrobe wouldn’t be complete without a stretchy,  sporty striped maxi dress.  Black and white are so chic, and of course, stripes are so popular because they have that wonderful nautical summer vibe.

Too big of stripes or too small can throw your proportions off, but I like this dress because the stripes are just the perfect width to be flattering. If you don’t usually wear maxis, try something new.  This dress is a classic that you will have for years. Great for poolside BBQs, at the beach, or on a cruise!