• Skip to main content
  • Skip to primary sidebar
  • Skip to footer

Nina Anders

Living an Ageless Life With Style

  • About
    • Privacy Policy
    • Cookie Policy
  • EBook
  • Shop My Favorites
  • Beauty
  • Fashion
  • Lifestyle
    • Inspiration
    • Morning Musings
    • My Almost Empty Nest

Why Women Over 50 Should Reconsider Dresses

10/22/2021 · In: Over 50 Fashion

This post is about dresses for women over 50-for fall and winter. How to choose the right dress and style it in several ways so you get the most out of your dresses.

I think dresses get a bad rap.  When I was In junior high school—they call it middle school now— the school board voted to allow girls and women to wear pants to school on Fridays.  Soon we were allowed to wear pants everyday, but we couldn’t wear jeans.  By high school, everyone was wearing pants and jeans to their hearts content.   

Up until that point, it was very unusual to see women wearing pants in public.   Over night, my friends and their mothers were  all wearing pants.  Pants were more comfortable, versatile and practical, everyone said.  Given that it was quite cold for most of the year where I grew up, pants were very popular, especially in the winter months.

While pants certainly have their place in our wardrobes, I have found dresses, to be the most versatile pieces in my wardrobe.  A very basic dress can easily morph from a day at work  to special occasions and from season to season with just a few shifts of accessories.  Adding a few good dresses to your closet will provide you endless options for a variety of occasions.

To this day, I prefer wearing dresses—especially living here in Florida.  What’s more, dresses can enhance or camouflage  one’s figure.  Dresses are great for creating optical illusions.  One can make all sorts of adjustments just by choosing the right shape, length, neckline and sleeve length and combine it with the right fabric—and you’d be surprised how different a woman’s body shape can look—no matter the body type.  With tweaks in the right place, dresses can look your figure look amazing, and really elevate your personal style.

We won’t be talking about the best sundresses here—many sundresses can be styled and worn right into fall though. In this post, I will share my fashion tips to help you get the most out of your wardrobe while accenting your best features and avoiding problem areas.  I will help you find a perfect dress or two to add to your wardrobe.

The Dresses You Need This Season

The Sweater Dress:  

Sweater dresses are a great classic style.  We often assume mature women can’t wear sweater dresses, but they actually look great on older women.  Look for swing style, wrap dress, look for an unstructured dress or a sleek body hugging number and you will not only look amazing, but will be warmer during the winter months.  This season’s midi length sweater dresses look amazing with knee high boots with a three inch heel.  Add a long coat , kimono, or cardigan to change up the look.  

On a cold day, try an oversized sweater over a maxi length sweater dress to create a warm, stylish a skirt and top. Add an interesting belt or scarf for a splash of color.  I love getting sweater dresses in solid colors as they are slimming, and elongating to the body.  Adding accessories will bring attention to your best feature, and should be a fashion staple. 

Floral Midi Dress:

This year we are seeing a lot of small florals and ruffles.  These look great in a midi length, and are great for creating an hourglass look.  Again, this style looks great with knee high boots, but a cute pair of booties work equally well.  This style often includes a flowy skirt which can be too much for many different body shapes.  If you want a sleek look, try to find a dress with fewer ruffles, and less volume.  (I must say, the massive ruffles we are seeing this season aren’t  a favorite of mine, but it looks great on many women, and if concerned about the cold, you can easily wear a set of silks underneath.  One thing about dresses with a lot of detail:  they are much harder to style multiple ways, however, a jacket with structure or a thick sweater can shift the look.  If you have a large bust, look for an empire waist, and avoid too much detail around the chest area.  Women concerned about their tummy can wear dresses with strong vertical lines, while women concerned about their hips can offset them with a wider shoulder and a belted clinched waist.  There are endless options!

Matching Skirt and Top Set:  

Erin Busbee showed one of this season’s matching two piece skirt and blouse sets and I loved it.  It looks like a dress, with a defined waist-which is very flattering and can be easily belted to add a little texture or accent to your waist.  In addition, the skirt and top can be worn separately to create a number of additional looks.  If you are looking for wardrobe versatility, this type of look will be great for you.

Wrap Dresses:  

Wrap dresses are one of those classic looks that flatters so many figures—and never goes out of style. These beautiful dresses have a way of drawing attention away from a problem afea—frankly, I think they are a perfect dress for women over 50.  Depending on how the wrap dress is made, you can sometimes style it as a kimono too.  This is another great look for mature women.

Evening and Party Dresses:

Let’s use a little imagination here—and steer away from the little black dress.  We all already have one, right?  Let’s go with something a little different this season’s party dress.  Sleeveless styles can be super versatile, and if you are worried about your upper arms, a beautiful faux fur shrug or a sequined number is just the ticket.  Best of all you can style the dress with a silk blouse underneath as well.  Evening is a great time to wear stealth dresses—they are one of the best dresses for an elegant evening look.  Sheath dresses in scuba styles can add structure  and are a lovely dress to wear.

Evening is often a time where we show a little skin—but as we get older we may be wary of showing too much skin—we should leave this to our discretion though—we all know the line between just right and too much.  

This Year’s Trends:

While floral prints are hot this season, animal print is still high on the list.   We are seeing a lot of ruffles—a carry over from last year’s Netflix hit Brigerton, though this season we are seeing lots of small florals on dark backgrounds.  Animal prints are still very popular and are a great classic print to add to your wardrobe.  We are also seeing brights, especially in faux leathers, which you might find in a two piece set or a bright statement jacket.

The midi length has taken the runways by storm, which is great for women over 50.  It is such an elongating look, and even looks great on petite women—just pay close attention to the length and elongate the line further with matching boots or shoes–avoid wearing booties and a midi or flats and a midi, though.

In evening wear, we are seeing mini dresses, but there are enough longer dresses to choose from as well. There will be something for everyone when it comes to festive party dresses.

Ways to style dresses:

As a young girl with an absolutely miserable wardrobe, I had to get really creative with my clothes.  I spent hours in my bedroom styling my clothing so I’d look more like the other girls in my school and like the outfits I saw in Seventeen Magazine.  Here are some of the tricks I still use to style my clothing.

Layering:  You can wear a t-shirt or blouse under a sleeveless dress, this is especially pretty when worn with a cap sleeve t-shirt under a slip dress. A fine gauge long sleeve sweater under a short sleeve dress is also a great look and a great way to extend a more summery style dress into fall and winter. It is a great option when you want to wear a sleeveless dress in winter..  You can also wear sweaters, blazers, evening jackets and cardigans over a dress to make it look like a part of a suit.

Don’t forget your button down blouses—I love wearing a silk blouse over a summer dress, and tying it at the waist, to define my waist and make another look from a dress.  It works best when one piece is a solid and the other is a print.

Don’t forget to consider shrugs, especially if you want to draw attention away from your upper arms.  Shrugs allow you to wear a variety of sleeve types while still covering a problem area. Look for interesting fabrics and faux furs to add to your collection.

Accessorizing:

I often add belts to dresses to change the shape of dresses, or just to add a pop of color or to add texture to the look.  Broaches, necklaces and faux collars and cuff sets are also great to have on hand as they can customize an outfit and convey your personal style.

Shoes and boots are a great way to shift a dress from season to season—as are handbags—a straw bag for summer, a leather bag for fall and winter, for example. Or boots vs strappy sandals–another super easy way to change the vibe of a dress.

I hold on to accessories even after they’ve gone out of style. I also invest in good pieces with the thought that I will keep it long term—I have a belt that goes all the way back to when I was eight years old, as well as several statement belts from the 1980’s. Styling older stand out piece with a modern outfit is the secret to really personalizing your wardrobe and elevating your personal style. 

In closing, I hope I’ve made a strong argument for the versatility of dresses for older women—any woman, actually!  Having a collection of great dresses and accessories can elevate your style considerably.  

By: Nina · In: Over 50 Fashion · Tagged: Best dresses for women over 50, Styling Dresses, women's fashion over 50

About Nina

Sharing A Journey is an award winning blog for women "of a certain age" who love life and style with a little inspiration mixed in. The blog and it's author Nina Anders has been featured in notable publications including Forbes, Next Avenue, Thrive Global and Parade. Photos by RSEsteyphotography Let's do midlife together!

you’ll also love

Nina Anders wearing blue floral swim coverupTHE Vacation Capsule Wardrobe Spring/Summer 2025
Nina Anders over 50 infelucener waring cream sweater and white pantsHow to Create Your Own Personal Style: A Guide for Women
Nina Anders wearing floral camisole and tan trousersTransform Your Wardrobe with the Seven-Day Style Challenge

Join the List

Stay up to date & receive the latest posts in your inbox.

Reader Interactions

Comments

  1. Suzanne Bell says

    10/23/2021 at 2:17 PM

    Great post Nina! I love dresses and agree that they are the most versatile pieces in my wardrobe – I even wear mine with pants and jeans! A wrap style is my go-to; but I love sweater dresses as well. One and done – out the door you go – my kind of outfit!

    xx
    Suzanne
    http://www.AskSuzanneBell.com

    Reply
  2. jodie filogomo says

    10/25/2021 at 10:31 PM

    I have become such a fan of dresses especially in the heat. It always surprises me that more women don’t wear them.
    The other place they are fabulous. On a plane because going to the bathroom is then much easier!!
    OXOX
    Jodie
    http://www.jtouchofstyle.com

    Reply
    • Nina says

      10/28/2021 at 8:01 AM

      I live in dresses over the summer and into the fall before it gets cool enough to wear jeans. thank you so much for stopping by!

      Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Next Post >

How Not To Dress Like A “Florida Transplant”!

Primary Sidebar

Meet Nina Anders

Meet Nina Anders
hello!

Welcome to Sharing a Journey! If you love modern classic fashion, videos about beauty and skin care with a little inspiration and lifestyle mixed in, you are in the right place! Grab a cup of coffee, and take a look around.

Read More

Connect

Categories

  • Beauty
  • Fashion
  • Inspiration
  • Lifestyle

Purchase A Copy of Graceful Transitions Here

Advertise

SiteGround Ad

Disclaimer

This site uses affiliated links in some of it’s posts.  Posts with affiliated links will be noted.  Sharing A Journey also receives gifted items provided for review.  When we have received an item for review it will be noted in the post.  As always, our opinions are our own.    Please stop by my About Page to read more about our policies such as copyright, disclaimers, and collaborations. Please Click Here for Our Privacy Policy

Buy Me A Coffee?

https://buymeacoffee.com/ninaanderssharingajourney

Follow Along

@sharing_a_journey

sharing_a_journey

Life and Style Blog | YouTube Channel

2025 is my year for a Glo Up starting with my skin 2025 is my year for a Glo Up starting with my skin care routine. I just started using the ZIIP Halo on my 65 year old skin.  Cant wait to see the results. #livingmybestlife #over60andfabulous #over50model #over65skincare @ziipbeauty
This week’s mini adventures had us in one of my This week’s mini adventures had us in one of my favorite spots-Dunedin Florida. We went for coffee and croissants at @dunedincoffeecompany where they have amazing coffee and a real in house bakery. Every so often the baker comes through with delicious creations right from the ovens. We went for some design inspiration @lrhome their shop never disappoints then on to the book shop. That made us hungry so we had to go to  @casatinas. How could you not?#livingmybestlife #over60andfabulous #over50womenoninstagram #over50style #outfitoftheday #over50model
I've been making a point to spend a lot less time I've been making a point to spend a lot less time on screens this year. It's been amazing how much free time I have to enjoy new hobbies and spending time with friends and family. I even tried my hand at painting with a Time For Art kit and actually made this sweet dolphin painting. I was surprised how easy it was even for someone like me who has very little painting experience. I loved how the kits came with everything I needed to make the painting, and I when I needed help, I watched a video on the Time for Art website. I thought it would be fun to host some friends for a girls painting night, invitations are in the mail--plus it would make a perfect gift. Be sure to check out @timeforartlive--I will link all their info in my link tree.
For the next 65 Days I am challenging myself to ch For the next 65 Days I am challenging myself to change a few bad habits and prioritize health, friendships and activities that enhance happiness and creativity.  I am looking forward to going into 65 and beyond healthier and happier than ever before. I hope you’ll join me over the next 65 days by choosing something you’d like to improve or a habit you’d like to break and see where it leads. #over50womenoninstagram #over60andfabulous #livingmybestlife
Instagram post 18020842631137506 Instagram post 18020842631137506
Instagram post 17901405167968170 Instagram post 17901405167968170
Follow on Instagram

Footer

On the Blog

  • Beauty
  • Fashion
  • Inspiration
  • Lifestyle

Info

  • About Nina Anders
  • EBook
  • Shop
  • Work with Me

stay in the know

Copyright © 2025 · Theme by 17th Avenue

We use cookies on our website to give you the most relevant experience by remembering your preferences and repeat visits. By clicking “Accept All”, you consent to the use of ALL the cookies. However, you may visit "Cookie Settings" to provide a controlled consent.
Cookie SettingsAccept All
Manage consent

Privacy Overview

This website uses cookies to improve your experience while you navigate through the website. Out of these, the cookies that are categorized as necessary are stored on your browser as they are essential for the working of basic functionalities of the website. We also use third-party cookies that help us analyze and understand how you use this website. These cookies will be stored in your browser only with your consent. You also have the option to opt-out of these cookies. But opting out of some of these cookies may affect your browsing experience.
Necessary
Always Enabled
Necessary cookies are absolutely essential for the website to function properly. These cookies ensure basic functionalities and security features of the website, anonymously.
CookieDurationDescription
cookielawinfo-checkbox-analytics11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookie is used to store the user consent for the cookies in the category "Analytics".
cookielawinfo-checkbox-functional11 monthsThe cookie is set by GDPR cookie consent to record the user consent for the cookies in the category "Functional".
cookielawinfo-checkbox-necessary11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookies is used to store the user consent for the cookies in the category "Necessary".
cookielawinfo-checkbox-others11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookie is used to store the user consent for the cookies in the category "Other.
cookielawinfo-checkbox-performance11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookie is used to store the user consent for the cookies in the category "Performance".
viewed_cookie_policy11 monthsThe cookie is set by the GDPR Cookie Consent plugin and is used to store whether or not user has consented to the use of cookies. It does not store any personal data.
Functional
Functional cookies help to perform certain functionalities like sharing the content of the website on social media platforms, collect feedbacks, and other third-party features.
Performance
Performance cookies are used to understand and analyze the key performance indexes of the website which helps in delivering a better user experience for the visitors.
Analytics
Analytical cookies are used to understand how visitors interact with the website. These cookies help provide information on metrics the number of visitors, bounce rate, traffic source, etc.
Advertisement
Advertisement cookies are used to provide visitors with relevant ads and marketing campaigns. These cookies track visitors across websites and collect information to provide customized ads.
Others
Other uncategorized cookies are those that are being analyzed and have not been classified into a category as yet.
SAVE & ACCEPT