Why Women Over 50 Should Reconsider Dresses

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.