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You are here: Home / image / Fashion Over 50 / The Most Comfy and Stylish Casual Dresses for Older Women in 2025
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The Most Comfy and Stylish Casual Dresses for Older Women in 2025

by Rebecca Forstadt-Olkowski 2 Comments

We all remember our mother’s comfy casual dresses when we were young before pants became popular. Some even wore poofy moo moos to cover up their middle-aged bellies. With more women working from home, including older women, 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 keep me 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?

The dresses below are designed to look sharp and will cover up figure flaws that most of us have as we age. Older women tend to have saggy arms, a protruding belly, or wrinkly knees. These will cover them and look chic as well.

This Karen Kane Artisan midi Dress is soft and comfy with a stretch waistline and can be used for casual and dressy occasions.

Karen Kane Artisan Dress
Karen Kane Artisan Dress

This Lands’ End indigo button-down midi dress is figure-flattering and is cool and breezy. It also has a stretch waistline so it won’t feel tight.

Womens Indigo button down midi dress from Lands End
Lands’ End Indigo Button Down Midi Dress

This Lilysilk Pinstriped Freesia Shirt Dress in Brown or Navy Pinstripe is chic and understated. It is loose fitting but the belt accentuates the waist to define your figure.

Lilysilk Pinstriped Freesia Shirt Dress Brown or Navy Pinstripe
Lilysilk Pinstriped Freesia Shirt Dress Brown or Navy Pinstripe

A pack of schmattes

I tried on this 3-Pack: Women’s Midi Short Sleeve Dress – Soft Elegant Dress with Elastic Waist for Women from Real Essentials on Amazon. I chose my set in Black, Pink, and White but there are multiple choices for color combinations. The dresses are made out of cotton jersey and will fit most figures.

You can layer them with a blazer, and they are perfect to take when you travel. I love to wear them around the house, to go to the store, or on relaxed occasions.

I ordered mine in XL as I have a tummy and they fit perfectly. I’m 5’2″ and the length hit me right at the knees which is perfect for me. For taller women, they may be shorter, just FYI.

3 PACK CASUAL MIDI DRESS BY REAL ESSENTIALS.

Order a 3-pack for yourself on Amazon here.

View more casual dress ideas below

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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