Comfortable T-Shirt Dresses For Women Over 50 That Look Great On

brunette woman over 50 wearing a floral t-shirt dresses and sandals

Comfortable, cute t-shirt dresses are a summer must-have for women. They are an easy one and done. You can be creative with the shoes and accessories you pair with them. What’s not to like about that?

However, not all t-shirt dresses are created equal. There are some things that I look for in a cute t-shirt dress now that I am in midlife versus when I was younger. I know that looking good in what we wear and age-appropriate makes all the difference. So today I am sharing what to look for in t-shirt dresses for midlife and beyond.

Before we dive into what makes great t-shirt dresses here are some other posts you might want to check out.

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Great T-Shirt Dresses For Women Over 50

T-shirt dresses can be appropriate for any age. Age is not an issue. They are great for casual looks instead of shorts in the summer. They can be dressed up to wear for dinner out or a summer soiree. I also like them for travel. Good knit fabrics tend to travel beautifully.

You can find t-shirt dresses in all lengths as well. So if you like to show off a little leg you can easily find short T-shirt dress. T-shirt dresses are also great in midi and maxi lengths. There is a style out there for each of us.

What To Look For In A Comfortable, Cute T-Shirt Dress

There are a few things that I look for when buying t-shirt dresses. Always looking my best even in casual looks means that I look for a few things to ensure I will be happy with them for some time.

  • Shape. Make sure that the dress has some shape to it. It doesn’t just hang straight. You want to have some interest.
  • Weight of the fabric. This is a biggie. I like to hold the dress skirt up to a light. Can you see through it?
  • Check the overall fit. You want to make sure that it fits correctly on the shoulders. The other important areas are the hips and bootie. You don’t want any pulling. Some women like to wear smoothing shorts like these under clingier fabrics. Another option many women love is this pair of shaping shorts. I like to wear a brief like this one under some of my summer dresses for a smoother look.

Where I Find The Good Ones

Over the years, I have tried many t-shirt dresses, and here are the best places I have found quality dresses that meet my criteria. I am petite so sometimes I will purchase petite sizing. Some brands don’t offer that and I still find some styles to work for me.

I am 5′ and usually wear a size XS. Sometimes I will wear an XXS if something is cut big. It is trial and error.


This brand knows how to make a great t-shirt dress. The Pippa is available in a short version like I am wearing above and in a long version. It is one of their iconic dresses that they make season after season. They just switch up the fabrics. Black is usually restocked throughout the season, but other fabrics come in and then they are gone.

Sezane is a sustainable brand so they do not make inventory in large quantities. The other thing about the brand is that they do not run sales. The quality of their fabric and construction is fabulous for the price point. I do not worry about it being see-through at all. How they construct the side belt detailing is so figure-flattering.
This coral floral pattern is the first Pippa to enter my closet and it will not be the last one. It is that comfortable and flattering.

Land’s End

This season Land’s End knocked it out of the park with some of their t-shirt dresses. They make a great weight of fabric that also has tencel in it. In case you are not familiar with tencel it is a fiber that is made from wood pulp. It is known for being soft, strong, breathable, and absorbent. All of those fabric qualities are good for the summer heat. You can also see me in another of their long t-shirt dresses here and a t-shirt midi dress here.

I think that you can see I am a fan of their dresses. Many of them come in regular, petite, and tall sizes which is wonderful. The long dresses make you feel like you are on a beach vacation even if you staying at home. So comfortable and easy to wear when you want an elevated casual look. Here are my favorites from Land’s End this season.


Ann Taylor Loft is always a good option for all styles of t-shirt dresses. You can always find on-trend styles and colors in their inventory. Most of the dresses are available in regular and petites sizing as well.

The dress that I am wearing in the photo above caught my eye because of the vertical striping and the colors. It is a soft brown stripe. The fabric almost feels like a seersucker to the touch which is interesting. The detailing at the waist is also figure-flattering.

Thanks, Let’s Keep In Touch

Thanks so much for stopping by today. I hope you found a new resource for great t-shirt dresses to add to your summer wardrobe. They are such an easy one and done for hot and humid days. It doesn’t matter if you are just around home or on vacation they are an easy thing to wear and feel put together.

If you enjoyed this post, you can also find me on Instagram and Pinterest. I would love for you to follow me there. I also have a newsletter that I send out every Wednesday and Sunday morning. In them, I share things that I don’t share on other platforms. I hope you will sign up by clicking here.

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