How to wear a short dress over 40

by Sylvia

How to wear a short dress after 40

I recently visited the US where I bought a fun naturally coloured dress at JNBY. I liked this dress because it has a lot of fun detail happening in the front and back. It was playful and trendy. But was it appropriate for a woman over 40? I wasn’t sure but the dress was on sale so I bought it anyway.

When my friend and I decided to go for lunch and go hunt for more fun places to take photographs in Singapore, I decided to wear it. I wanted to add to my previous post on wearing more colour so I chose to wear this dress with my new red high heels, added a belt, a coloured watch and voila! My plain coloured dress now looked very colorful!

But there was still the issue of the shortness… However, I felt good that day and since we were going to do a little bit of a ‘photoshoot’, I decided to wear the dress as it is. There are no strict rules when it comes to dressing over 40, but some could argue that this dress is a bit too short for me. On the day though, I felt good and had fun, so I think I got away with it.

Over 40 fashion - short dress

Wearing a short JNBL dressPhotos by Anja van der Vorst

But it also got me thinking. There are days when I may not want to show my legs and dress a little more lady like. So how can you and I wear a short dress like this on all occasions? I played with a few options:

1. In the first picture you see me wearing the dress with skinny white pants. This is quite a funky and sporty look.

2. In the second look I combined the dress with a black skirt. This is a far more elegant lady like look.

How to wear a short dress after 40

3.  The third look is possibly my favorite alternative. The dress is combined with striped long pants and high heels. This look makes me look tall, trendy, yet very elegant in my opinion.

JNBL dress with pants

So this proves that you need not necessarily leave a great dress that may be a little too short for you in the shop. On certain occasions you can wear it as is, but on others there is just so much you can do with a wonderful short dress.

How about you? How do you wear short dresses? And what is your favorite look of the ones listed above?

{ 22 comments… read them below or add one }

1 Acorn

I love the way your pair dresses with pants and was wondering if you have any suggestions for a cold weather version. What kind of top layer do you think might work – would a short cardi look too choppy? How about shoes, would boots work with a dress over pants? Thanks, love the blog!


2 Sylvia

Hi Acorn! There are actually quite a few nice dresses in the shops now with long sleeves and if they have a bit of an A-line, they would be perfect with wider pants as in option 3. Another option is to wear the dress (especially more straight dresses) with leggings or thick tights. Combined with boots, that would be a very hip look. The top middle look in this post is a good example of that. Another idea is to pair a dress with a longer cardigan (like almost the same length as the dress), but in many cases a short cardigan will work as well. I think you can have a lot of fun with dresses and layering in winter. I’ll try and show some examples later some time.


3 Vicki Davisson

I like the third look too. The colors blend better and the shoes tie it all together. Well done!


4 Sylvia

Thanks Vicky!


5 Jeannie

I thought you look fab in the dress alone!
Found your blog from +40 list from the Citizen Rosebud.


6 Sylvia

Hi Jeannie, Thanks for stepping by and commenting. I visited your blog as well. You have great style! Also cannot believe you are already 50, you look so young. Wanted to leave a comment but couldn’t. Have you disabled comments for your blog?


7 Irina

You look fine in just the dress. I don’t think it’s the years that matter, but the actualy appearance. Some girls at 15 wouldn’t be able to pull it off.


8 Sylvia

Thanks Irina! That is true, but I still prefer my skirts and dresses a bit longer these days….


9 Jean at Dross into Gold

Another home run in the hot-weather-fashion blog series!!! I love all of these iterations and would incorporate them all into my wardrobe. Watch and behold…I feel my fingers itching to start sewing. Thank you so much. You look incredible.


10 Sylvia

Thanks Jean. You’re very lucky that you can sew. You will be able to create the most original creations!


11 Petra

I love that dress, but I do prefer it used as a tunic, especially with the black skirt – very sophisticated. I do love it with the red accessories the best, as red looks great on you; I wonder what it would look like with a dark red pencil skirt and black shoes, black chunky necklace and a red bag? Hmmm…..


12 Sylvia

The dress is pretty fun. I just cringe at the above pictures now…. Yes, it’s better as tunic and best with colour accessories too. I think it would look great in the outfit you suggest. I’m still looking out for a great red skirt!


13 Diane

Love the dress in every way you have shown it. I think a woman over 40 can certainly carry this look if she carries herself with pride in it. Your legs are toned so that helps with the look… I’m nearing 60 so doubt I would try this… unless with the black skirt or a pair of slacks as you have shown it. Very nice!


14 Sylvia

Thanks Diane. I think that the dress / tunic over pants (or other skirt) look is great for women over 50. Have fun experimenting with the look!


15 Greetje

Found this “old” feature of you today and I think you do not have to cringe at the top photos. You look really nice. Good legs. And yes it is short, but you can still get away with it. No worry. And you know I am always honest.
Enjoy a short dress once in a while and don’t dismiss it as in 10 years from now, you cannot do this anymore.
I like the bottom outfit with the striped trousers too. Very nice. But missing the colour here.
Actually liking everything, dress, shoes, necklace, belt.


16 Sylvia

Thanks Greetje! As you know I will still wear some short dresses in my summer holidays!


17 Habit

Hi Silvia
It is my fist time in your blog and I think it is really great with useful tips and ideas relevant to me.
You look great in the dress and the red accessories. It looks you feel very comfortable and natural in it.
I encounter the question of “too short” many times as I am tall and have many short dresses.
To keep a “dressy look״ my solution to this is to wear a combinezon-like dress under the dress, so I gain the extra length and the nice twist. There are many nice ones with interesting prints or laces that do not look like the old fasioned ones.
I like best your combination with the black skirt.


18 Sylvia

Thanks for your feedback Habit! Yes, you can come up with very creative solutions. I often combine short dresses with pants with is still a favorite and you can find many more examples in the what i wore section (under style tab) on this site.


19 Sabina @Oceablue Style

Hi Sylvia, I just love your style section here and like coming back for ideas! I feel quite comfortable wearing short dresses and skirts and I guess thats what tells you if its right or not. Maybe you would like to check out my post here with about that little bacl (short;-)) dress. Sabina


20 Sylvia

For sure Sabine. You look smashing in your short dress!


21 Sabina @Oceanblue Style

Sylvia, thanks so nice of you to say! You know I posted our Radiant Orchid Coll. with a reference to your blog, right? Have a great day, Sabina


22 Danica

Even those so called acceptable dresses above are too short regardless the woman’s age!!!! They need to be an inch or 2 longer. Above the knee is still too short. Knees should be somewhat covered to have an attractive look. The designs have been very bad these five years. So hard to find a decent skirt that is not too patterned and made from good quality material – not this thin stretchy leggings material. Dresses are designed really badly- too wide necklines, too tight bodices and of course too short. It’s like they were made for some alien type of bodies. Where has the sense gone from these manufacturers? What happens? It takes long to sell those crappy dresses/skirts that they end up in clearance.


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