Best Midi Dresses for Women over 40 to Style for Fall

After many hemlines trending north of the knee (read: short), we are finally (finally!) starting to see them turn south again.

For over 40 gals, this doesn’t come a minute too soon. While I’m not averse to showing off your gams, many women aren’t comfortable in a dress so short that just sitting down or bending over to pick something up requires them to be contortionists lest they reveal too much.

If you’re thinking about pulling out some of your midi-dresses from days gone by that are still hanging in the back of your closet, think twice. Today’s midi-dress is about more than simply being long. Here are a few modern midis and ways to style them so you look fab, not frumpy, this fall.

Black and White Stripe Midi Black block Heel


1. Look for Sophisticated Design

Leave behind the flounce, ruffles, and calico prints on the midi-dresses that we wore way back when. Those 70’s style midis can make you look like you belong on Little House on the Prairie.  Instead, look for sophisticated designs like this off-the-shoulder fit-and-flare dress in bold black and white. The high contrast colors and trendy neckline give this midi a very modern update.

Cheetah Midi Dress Black Leather Booties


2. Choose Figure Flattering Silhouettes

The shape is important when you’re wearing a dress made from a lot of material. That’s why I like this animal print wrap dress by DVF.   The way it nips in just at the waist is incredibly flattering. If you have a small waist, it really shows it off, and if menopause has made your waist disappear, this dress gives the illusion that you’ve still got one. I love the leopard print too. It’s a popular print this fall.



3. Wear Sumptuous Fabrics

Midis are elegant, and a velvet tea-length midi is as elegant as you can get. I love the rich look and feel of this soft, sumptuous dress. It’s such a refreshing change to find a dress that has long sleeves for fall and winter!

Floral Midi Navy Pumps


4. Try a Print Midi Dress

The thought of a floral midi dress may conjure up visions of old lady style, but take a look at this striking print sheath dress, and I’m sure you will change your mind. The gorgeous winter floral print with oversized blooms is feminine and sophisticated. Accessorize it with a burgundy-colored clutch and some simple black pumps, and you have a timeless look that gives you a little extra leg coverage.Black Bell SLeeve Midi Floral Clutch

5. Experiment with New Details

Never underestimate the power of a trendy new detail like boho flare sleeves to give a fresh new look to your outfit. The simple but sweet maxi dress with its flare sleeves is easy to wear and looks right in style!

Are you going to buy a midi this fall, and how will you wear it?

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9 thoughts on “Best Midi Dresses for Women over 40 to Style for Fall

  1. Hello,

    These dresses are fantastic ic. I do, however, notice that I look very old and frumpy when I wear my midi skirts and fedora hats. My s oes are flat many dresses have very busy prints of flowers or solids.
    What can I do so I will not seem older than I am and stop looking frumpy? I am in my 60s; I lo the length of the midis and the look of the many hats I own.

    Thank you for your time, and have a great holiday.
    Laura Cerebella

    1. Hi Laura, I don’t know what the dresses look like, but I would question the cut and the fit. You will look frumpy if it is a loose cut and fit. I’d go for something that follows the lines of your body and is more streamlined. Also, small florals can age. Try medium florals in modern color combinations. Here are some new spring colors:https://www.fabulousafter40.com/spring-summer-2020-color-trends-pantone/ Finally, consider your accessories as they are the quickest way to update your look. This is particularly true when it comes to your bag and shoes. If you want some inspiration, google midi dresses on Pinterest, and up will come to all kinds of visuals that will give you some modern styling ideas:https://www.pinterest.ca/sasiavisasi/midi-dresses/ Best wishes, Deb

  2. Like flared crops, many styles need time for the eye to get used to. The midi has been around a while; somehsomehowes received the dowdy label. You did an excellent job with your outfits; I would like to see some more casual wear. I think most women do not look good in a mini. The knee is not the most memorable part of a woman’s body.

    1. You can wear almost any shoe, including sneakers! The hardest part of wearing a midi is the length where it hits you on the leg; just like crop pants, it needs to be tailored to what looks best on you.

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