Casual summer dresses for women over 50

Finding casual dresses for women over 50 can be a challenge. This post shares beautiful dresses that you can wear and feel comfortable in at any age.

Spring and summer bring with them not only warmer weather, good fruit, time off school, and vacations but tons of events that require a dress.

Things like laid-back weddings, baby and wedding showers, and graduations fill up your calendar. It’s a fun time, but figuring out what to wear to everything can be a challenge. Casual dresses for women over 50 are hard to find with all retailers focusing on women in their 30s and 40s. It can be confusing to choose a dress that feels appropriate.

I’m here to tell you that you can wear anything you like. This isn’t a list of what not to wear, but a list of so many beautiful things that you can feel confident wearing.

I’m building on last week’s post about shoes to wear with long dresses. I’ve added in the dresses this week. Next week I’ll include all the accessories so you can have several outfits to choose from.

You can dress each of these up or down with shoes and accessories. All are great casual dresses for women over 50 options.

What’s the best length for women over 50?

Whatever length you are comfortable with is my answer to this one. But many of my 1:1 clients who are over 50 prefer something on the longer side. The dresses that I’m sharing with you today are long. They are all maxi dresses that are everywhere this season. If you’re petite and don’t feel comfortable in a maxi dress consider opting for a midi style instead.

Let’s take a look at the dresses I’ve selected to go with those shoes, shall we?

The floral maxi dress

The bright pops of color in this dress allow you to add any number of colorful shoes. I selected a pair that have a few colors from the dress. The open heel on the shoe has an airy effect and creates some balance for this large-scale pattern.

bold colored large scale floral dress with ruffles at sleeves and faux wrap. One of the casual dresses for women over 50 featured
Open heeled wedges/ floral maxi dress

A monochromatic look

This spruce maxi dress is so pretty and simple. I love that it comes with a removable belt. You can replace it with a leather one or wear it loose with slides.

I paired it with the deep green leather sandals for a tonal look. This would also be great with a neutral sandal or metallic heel.

spruce green dropped tier maxi dress.
Dark green leather sandals/ spruce colored maxi dress

Straw colored maxi

This straw-colored striped maxi dress makes a great option as it has a defined waist. Something that is important in creating that hourglass shape. The v-shape at the neck is also an important detail in this garment and very flattering to many body shapes. I added the rose gold floral slides for a pop at the end of a neutral dress. Raffia sandals or a contrasting color would look great with this dress as well.

straw colored striped dress with large elastic at the waist. One of the casual dresses for women over 50 shown in this blog post.
Straw colored maxi dress/ rose gold floral slides

Petal and green caftan

I like that this caftan has a slimmer cut to show your shape. The colors in this are gorgeous with stripes and patterns so I decided to go with a neutral pair of raffia slides. The asymmetrical shape is all the detail these shoes need, you don’t want it fighting with your dress.

posey and green colored striped and multi=patterned slim cut caftan.
Petal and green caftan/ raffia slides

The bold caftan

This bold pink with orange detail caftan is darling. I do love this style for spring, even though there isn’t any definition at the waist. Sometimes you need to wear something loose, but still have it look good. This is the perfect solution for those times. I selected the multi-colored wedge, but would also love to see this with a shoe in orange to go with the piping.

Pink and orange caftan/ open heeled wedges

The tiered maxi dress

The red tipping on this powder blue dress is unexpected. So are the sweet floral embroidery details. I decided to lean into the feminine wiles of this dress and add the pearl kitten heels. This is such a sweet look.

Blue tiered maxi dress/ pearl kitten heels

Black and white for summer

Another LemLem caftan with a slim silhouette. I paired this with bold dark shoes for some contrast and a more formal look. But this dress could easily be worn with leather flip-flops to the pool.

Black and white caftan/ raffia block heel

One-shoulder casual dresses for women over 50?

I get asked by my 1:1 clients all the time, can I show my arms? I always say it’s up to you. If you feel comfortable doing so then go for it. This dress is a beautiful option for doing so. I love this color and decided to put a cerulean blue sandal with this dress. The solid fabric allows you to have some fun with the accessories.

One shoulder dress/ blue wedge heels

Vertical and horizontal stripes

This striped dress has stripes going in all directions. This contrast makes the dress more interesting. I also decided to add a pop of color to the shoes. But I didn’t stray too far from the dress’s preppy nature by adding pink shoes. Metallic pink to be exact, but it definitely makes for an interesting detail in the outfit.

Striped dress/ pink metallic kitten heels



I show women over 50 how to get noticed, stay relevant, and be connected through their wardrobe. Getting dressed is something you have to do each day, why not make it fun.



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