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 dress Photos 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?

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{ 16 comments… read them below or add one }

Acorn September 27, 2011 at 5:23 pm

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!

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Sylvia September 28, 2011 at 4:45 am

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 http://40plusstyle.com/how-to-dress-the-rectangle-body-shape/ 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.

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Vicki Davisson September 28, 2011 at 3:18 am

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

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Sylvia September 28, 2011 at 4:45 am

Thanks Vicky!

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Jeannie October 30, 2011 at 1:55 am

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

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Sylvia October 30, 2011 at 8:03 pm

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?

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Irina April 4, 2012 at 2:45 am

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.

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Sylvia April 6, 2012 at 12:09 pm

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

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Jean at Dross into Gold April 9, 2012 at 10:53 am

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.

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Sylvia April 9, 2012 at 12:59 pm

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

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Petra May 9, 2012 at 3:31 pm

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…..

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Sylvia May 9, 2012 at 6:33 pm

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!

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Diane June 26, 2012 at 4:38 am

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!

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Sylvia June 29, 2012 at 12:18 pm

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!

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Greetje August 2, 2012 at 3:17 am

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.

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Sylvia August 2, 2012 at 4:55 pm

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

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