The hotter weather is ideal for the topic of casual summer dresses for women over 50. In fact, this was a recent discussion with a group of older women about how dresses don’t have to be thought of just for dressy events anymore.
Casual is the name of the game in our society, and there are a ton of reasons you might want to incorporate casual summer dresses.
Quote of the day: “Just because it didn’t work doesn’t mean it was the wrong choice. The world is full of probabilities, not certainties. Find a game where the probabilities favor you and keep taking shots.” James Clear
Casual summer dresses for women over 50
1-Why wear a dress?
2-Maxi dress for women over 80
3-Knee length dress for women over 70
4-Midi length casual summer dress
5-Other inspiration
Now that women CAN wear pants (as opposed to over 50 years ago when Lesley tells the story that she got sent home for wearing culottes to school), you find that many women over 50 don’t wear casual summer dresses. And it seems a shame because there are many advantages to them.
Since the motto of this blog is to provide you with variety, the three of us are showcasing casual summer dresses in a variety of lengths and styles.
It goes to show there is something for everyone.
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Related post: How many dresses should I own?
Why Wear a Dress?
Gone are the days when the idea of wearing a dress means you need to be going to a fancy event. There are so many casual summer dresses for women over 50, and the reasons to wear them are endless. But I’ll give you my top three!
1-One and done. This saying is used all the time with dresses meaning you don’t have to think about does this top go with these bottoms? There are no questions about should I tuck in my top, or is it the right proportion. You put on the dress and are good to go.
Of course, in a fashionista’s world, there are accessories to add to the overall look, but in real life, maybe you just put on your shoes and head to the grocery store.
2-Cooler for the hot days. There is no disputing that a floaty dress can give the air circulation that is ideal for any hot, summer day.
Insider tip: If you struggle with “chub rub” there are many who suggest shorts to wear. However, I think that negates the idea of having that air circulation. Therefore, the anti-chafe sticks (found on Amazon) may be better for the job.
3-Bathroom breaks. Now let’s talk reality. As we get older, we think about how easy it is to go to the bathroom in what we are wearing. It’s just a fact of life. So that’s why this is one of the reasons you should consider wearing casual summer dresses.
Just think how much easier (and faster) it is to pull up your dress and not worry about it puddling on the bathroom floor full of germs.
In fact, it’s truly one of the reasons, I consider a longer dress the IDEAL travel outfit (both on a plane and for a road trip). I’m still flummoxed about why more women haven’t embraced wearing dresses or skirts for travel. (How do you like that word?? Who knows how it came to me, haha).
Of course, there are certain dresses that fall into the casual summer type better than others. Yet, since one of my superpowers is to make your closet versatile, I challenge you to make some of your dressier dresses work for a casual day. (Cathy, I’m talking to you with this dress)
What Makes a Dress Casual
As a quick aside, let me give you what I could consider the details of casual summer dresses. Of course, the list is probably endless.
1-Material selection. Your knit materials “seem” more casual than your silkier materials. But don’t let that detail stop you from wearing some of the silkier dresses for a casual day. In fact, my dress below is the perfect example of that found in the midi dress section of this article.
2-What you wear with it. The shoes and even your accessories can take a dress and make it seem either more casual or more dressy.
Maxi Casual Summer Dress: Charlotte
Let’s talk about the maxi casual summer dresses for any women over 50. My mother made this dress ages ago, and the coolest thing about it? It’s reversible. Here is what it looks like showing the other side.

Dress: My mom made it-it’s reversible~~ Shoes: Impo~~Scarf: Mom made it ~~ Necklace: thrifted~~ Earrings: thrifted ~~ Purse: Enzo Angiolini-thrifted
The color of the dress is such a stunning color for any time, but especially in the summer. This blue side is a very small blue print, yet most of us would see it as a solid color.
Here’s the thing with maxi dresses. They can seem to be overwhelming if there is a lot of fabric. That’s why in many cases, you will see them with some other kind of skin showing.
Sometimes that is a “v” neck or a slit up the side of the skirt.
But that doesn’t mean you can’t wear a maxi that doesn’t have skin showing.
Insider tip: If you have a maxi dress and can’t figure out why you don’t love it on you, think about how you can change it up. For example, when Lesley pulled up some of the material on her dress and attached a flower pin to it.
Remember: You are the boss of your clothes.
Another option is to have a slit added to the skirt portion. It would be an easy alteration.

Belt Action
Wearing a belt is one of those controversial options for many women as we age. Over and over I hear the conundrum that the waist is not the part of the body someone wants to accentuate.
Okay, I get it, but let’s stop and think more about belts. Sure, some belts will cause you to notice the waistline. Yet sometimes, they can be worn to give the clothing more shape without being the focal point.
For example, this clear belt that Charlotte is wearing (here is one similar on Amazon).
One of the secrets to having a belt help pull in extra material without being the focal point is to keep it relatively loose. You don’t have to pull it super tight. And then make sure to adjust and fix the extra material so it’s not bunching all in one place.



Accessories for a Casual Dress
Since Charlotte’s dress is a crew neck, she used her long necklace to create the idea of a “v-neck” opening. It is also the way she added more color to the overall look.
Take a quick gander at the scarf hanging from the purse too because that was made with the leftover material from the other side of the dress.
We don’t often think about wearing our scarves in the summer months, but hanging them over your purse to be there in case you need a layer for the air-conditioning is brilliant.
Shoes are another factor that will help the casual summer dresses vibe for women over 50. You don’t have to wear heels with any dress anymore, so bring out the flats meaning ballet flats, sandals, or sneakers.
And the shoes DO NOT need to match the dress. Have fun with bringing in a totally different color.


Knee Length Summer Dress: Lesley
Lesley shared that casual summer dresses like this one are not only perfect for shopping or lunch, yet she will also wear them around the house.
Does anyone else remember your grandma wearing “house dresses?” There was a good reason for them.
This is proof that they are easy and comfy!

Dress: Nine West-Kohls ~~ Shoes: Clarks ~~ Scarf: no label (bug repellent)~~ Necklace: SteinMart~~ Purse: no label-thrifted~~Hat: no label
This tiered style of dress is everywhere right now. In fact, you just saw all three of us showcase the same one in different colors last week.
There is the dilemma that the shape doesn’t make it flattering. But I had a bunch of comments that reiterated my thoughts that “flattering” is overrated. Maybe it’s not the most slimming dress ever, but who said slim is our ideal standard?
I think we would be much better off if we were ambassadors of being kind and looking nice instead of taller and thinner.
Insider tip: If you are looking for a tiered dress that is more shape enhancing, then concentrate on the ones with a more fitted top or waist definition.




What to Wear with Casual Summer Dresses
The accessories can add so much personality to our overall look. And for this salmon-colored dress, Lesley added a shell necklace. And since shells remind us of the beach which is a summertime vibe, it’s fabulous.
It’s also a perfect addition to the neckline as it follows the shape of the “v”. Then again, it would work just fine for other necklines too.
The outfit also boasts some straw details which is another summer vibe detail along with the fact that it tends to make it seem more casual. This round straw purse always gets tons of compliments and Lesley loves it because it’s big enough to pack with all of her stuff.
Then the shoe choice was one that matched the dress and was easy for the day. Flip-flops are acceptable to wear for the day and definitely make the overall look more casual.
Insider tip: If you talk to any podiatrist, they will warn you against wearing flip-flops for consecutive days in a row. It’s hard on your feet because your toes have to curl and grip to keep them on. So make sure to alternate your footwear choice.


Midi Casual Summer Dress: Jodie
Now let’s talk about anything between the maxi and shorter casual summer dresses. I always joke that I’m an equal opportunity clothing lover. Why only limit ourselves to one length of skirts and dresses??
Having a variety in our closets allows us to be prepared for many different events and occasions.

Dress: SteinMart ~~ Shoes: Walking Cradles ~~ Belt: Target~~Earrings: Francescas~~ Purse: Ideas Valyen -won in a giveaway ~~Hat: Brooklyn Hat Co~~Glasses: Glasses Shop
I am showing a midi-length version of casual summer dresses for women over 50. I have come to love this length more and more. Why? Maybe because they are easier to sit around in and you don’t have to worry about flashing others when wearing them.
Insider tip: This length is also beneficial when you are getting into a car. Your legs are protected from the H.O.T. leather seats.
What I’d like to point out is I found this dress during SteinMart’s going out of business sale. It was $5. The secret? It’s 2 sizes larger than what I normally wear. Does it look too big? Maybe. But I will tell you that is one of the factors that makes it so comfy on our 100+ degree days.
Insider tip: Don’t obsess and focus only on “your” sizes when shopping. Sometimes the best items can be in a different section.

The Details
I did wear a belt with this dress, but there have been times I’ve worn it without. It’s definitely a floaty dress without the belt. In fact, the dress came with a self-belt which I immediately took off and hung with the rest of my belts.
This woven belt has been a wonderful surprise. I was influenced by a friend on Instagram to buy it and I’ve worn it a ton.
The style of this dress calls for a strapless bra. Either that or you could wear a navy racerback bra and it might blend in nicely.
Not surprisingly, I wore my Gatherall bra. Not only is it strapless, but it’s also cooler than a normal bra since there is no material wrapping around your body.



Neutral Accessories
Lesley and I didn’t plan to wear straw accessories together. But it is the season, right?
I’d also like to point out that I really added in most of the colors in my dress.
Blue-the hat
Bright pink-the earrings
Yellow-the purse
Insider tip: You don’t have to match all of your accessories to each other for the look to be cohesive. Play around and have fun.
Since the temperatures are rising, I don’t often wear statement necklaces, but I thought I’d give my delicate ones some love. It’s nice because they add a little bling, but you don’t really feel them.
And the crochet sandals are from Walking Cradles a couple of seasons back. Does it mean I like them a lot if I have them in both this version and the shorter version?? I wear this height when I don’t have to walk as much, and the other ones for all-day walking. The proof is how I wore them on many of our excursions on our cruise.


Other Casual Dresses for Women over 50 Inspiration
Dresses can be such an easy clothing item to wear for women of any age. So let me show you many of the other times we have worn dresses even for casual days.
Here are some other dress inspirations
1-Dressing for your body shape
2-Same dress worn for different occasions
3-Wardrobe essentials
4-Dress up a casual dress
5-Matching casual summer dresses

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