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You are here: Home / image / Fashion Over 50 / Comfortable and Stylish Casual Dresses for Women Over 50 in 2026
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Comfortable and Stylish Casual Dresses for Women Over 50 in 2026

by Rebecca Forstadt-Olkowski 2 Comments

We all remember our mothers’ comfy, casual dresses when we were young, before pants became popular. Some even wore poofy mu-mus to cover up their middle-aged bellies. With more women working from home, including women over 50, it’s not always easy to find comfortable dresses that do not look frumpy.

I have a few dresses I love to wear around the house because they’re cool and breezy. I call them my schmattes. That is the Yiddish word for rags, and I wear them until they fall apart. We often think of a schmatte as something our grandmother wore, but these days, women over 60 are nothing like our grandmothers. We can be sexy, business-like, or casual, but why limit ourselves to pants?

Older women want to cover up the figure flaws that most of us have as we age. We tend to have saggy arms, a protruding belly, or wrinkly knees. Some of the suggestions below may help you choose a style that’s right for you.

This classy vertical stripe dress from Lands’ End is made of 100% Supima Cotton and can be worn for a casual or dressy occasion. It also makes an excellent travel dress.

Lands' End Poplin Midi dress
Lands’ End Poplin Dress on Amazon

Linen is always breezy and confortable and you don’t have to worry about wrinkles because they are part of its charm. This linen dress by Eileen Fisher gives you plenty of room to move and still look stylish.

Eileen Fisher linen loose dress
Eileen Fisher Washed Organic Linen Dress

Pintucks can be very figure-flattering as they subtly define the waist without squishing. This Old Navy Pintuck Waist Midi dress comes in black and light blue and can be dressed up or dressed down depending on the occasion. It is an excellent basic dress.

Old Navy Pintuck Waist Midi Dress
Old Navy Pintuck Waist Shirt Dress

You can’t go wrong with this cotton Ava midi dress by Boden. It also comes in a purple tone. You can wear it around the house, to a lunch or tea, or when you travel.

Boden Ava Cotton Dress
Boden Ava Cotton Midi Dress

I love my Quince Vintage Wash Tencel Midi Dress. I don’t have much of a waist, but it helps define it. It’s comfortable and cool in warm weather. The dress comes in two other colors.

Quince Vintage Wash Tencel Midi Dress
Quince Vintage Wash Tencel Midi Dress

Do you have a casual dress you love to wear? What does it look like? Please leave a comment below.

House Dresses

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Filed Under: Fashion Over 50, image Tagged With: dress, fashion over 50, shopping, style over 50

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About Rebecca Forstadt-Olkowski

Rebecca Olkowski is a travel/lifestyle blogger and founder of BabyBoomster.com, for active older women over 50. She is a purveyor of all things fun, loves to venture out in the world, is a foodie, and lives in Los Angeles.

Comments

  1. Carolyn Lee Arnold says

    June 2, 2022 at 9:55 am

    Hi Rebecca! Great update of the dresses! I love the variety of lifestyle infusions that you offer women over 50, from trips, to clothes, to thoughtful commentary about all the options we have about where and how to live. I loved our interview – thanks for supporting my book, Fifty First Dates After Fifty: A Memoir. It is doing well, and I send thanks and love and Happy Summer to you!

    Reply
    • Rebecca Forstadt-Olkowski says

      June 2, 2022 at 9:58 am

      Thanks so much, Carolyn. It’s great to hear from you. I’m so glad you are enjoying my site and I had fun with our interview as well.

      Reply

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