How to Confidently Wear a Short Dress Over 40, 50+

Have you ever seen a cute dress and wanted to buy it but it seemed a little too short? Sometimes there are ways around this problem. Here’s what I did with mine, plus a few other style tips for how to wear a short dress over 40, 50+

Let me begin by saying that skirt length is a personal choice. I’m not here to tell you that you should or shouldn’t be wearing short dresses as a mature woman. The days of judgment and “age-appropriate dressing” are over. Style now is about what makes you feel confident, and that usually stems from wearing something that is in tune with your personality, your figure, and lifestyle.

Myself, I’m fairly conservative, and I typically like my dresses to land at the top of my knee, but there is the odd time I feel like wearing a dress that is more casual, fun, and sassy. In this case, I may buy a shorter skirt, so long as I can find a way to feel comfortable in it.

Take this cute, green dress, for example.

I fell in love with the clean, modern look of this fabulous Blouson-style stretch jersey dress. It’s easy to slip on, it’s soft and super comfy, and it’s casual, although you can dress it up if you want to. Yes, it’s on the short side, but that brings me to the first point I want to make about styling a short dress over 40.

1. Consider the Overall Dress

This dress may be a little short, but it also has a high neckline (I love that stunning bateau neck!), and it has long sleeves, so it isn’t that revealing. If this dress had a V- or scoop neckline, or was sleeveless or had short sleeves, it would have felt too bare, and I wouldn’t have bought it. The overall style makes it work. Add to this that my legs are still one of my best features, so why not have a bit of fun?

There are a few ways to make a short dress work at 40, 50 +

2. Wear Opaque or Semi-Opaque Tights

Short dresses are a little easier to wear in fall and winter because you can create the illusion of a longer hemline by wearing dark, opaque, or semi-opaque tights. My dress is dark green, my tights are black, and you don’t notice the hemline as much as you would if I wore bare legs or sheer stockings.

3. Wear Flat Shoes or Boots

The higher the hem,  the shorter your heel should be.  Flat or low heel shoes or boots help make your short dress look less short. This works even better when your footwear and tights are the same color. I’ve paired low-heel black boots with black tights. There is no color break to draw attention to my legs or my short hemline. My dress is also a dark color which also helps.

4. Wear  Leggings with a Short Dress

If your short dress is a straight shirtdress, tunic style, or is flowy, you can often wear it with leggings. (See examples here). Leggings don’t work so well in this case because my dress tapers in at the bottom a little too much.  You want your dress to look like a long top over leggings, not a short dress over leggings. One type of dress that always looks fabulous with leggings is a short sweater dress. (Here are some examples)

5. Layer a Long Cardigan with a Short Dress

Another thing you can do to offset the shorter length is to wear a long cardigan over top of a short dress.  Cardigans are traditional and soften the sexy look of a short dress. Plus, when you wear a cardigan that is a little longer than your dress, it creates the illusion of length.  Note: too much of a difference in length will emphasize how short your dress is, especially if your cardigan is in a contrasting color to your dress like this red one!

shop the look

Finding a way to wear a short dress over 40, 50+ takes a little trial and error but can sometimes work. So if you have a short dress hanging in your closet that you’ve given up on,  or you have your eye on a short dress you’d love to buy, play around with these ideas and see what you think. You might just be surprised by the results. Now go rock that short dress!