Questions and answers on dressing after 40

by Sylvia

Questions and answers on how to dress after 40

Women arrive at my site through a lot of different questions. Of course many of these questions are already addressed and you can see some of the most popular ones on my category page on how to dress after 40.

But here are some more specific questions from (new)readers that I would like to respond to today.

Can you wear a body con dress after 40?

Of course you can! Body con dresses can look fabulous at any age. They are especially good for the hourglass body type and great for showing off your delicious curves.

However, I would personally only wear one if you have a great body to show off. I feel far too self-conscious in a body con dress as every body flaw I have is highlighted. I have a very flat bum that is rapidly going south, so a body con dress does not look all too flattering on me or others that have the same issue.

In the end though it’s up to your own figure flattering priorities. If you like to wear a body con dress even though your body may not be in tip-top shape, you can consider getting one with a print. Prints are very good at camouflaging and you can get away with a lot more. Another trick is to smooth out your body with shape wear.

How to wear shorts over leggings

I would say: don’t. I don’t find this a very good look at all. Here are some more tips on how I DO think you should wear leggings after 40.

How young can a 40+ woman dress

As young as you feel! I don’t think there are any clear-cut answers to this, but if the image in the mirror reflects how you feel and corresponds with the message you want to give the world, then just do whatever you want.

However, if you desperately like to hold on to something you are not, it will not look good. In general I feel that women over 40 look better (and younger) if they apply some of the following 10 tips.

How to wear a miniskirt with boots in your 40s

I would say, keep the look as chic and classy as possible. Choose good fabrics and make sure you wear high quality boots. This outfit will also look better if your boots are snugly fit around your calves. Consider the length of your miniskirt as well. I would say that longer is most often better.

How to wear cowboy boots in your 40s?

Keep it classy. I would not wear them with short skirts or shorts but rather pair them with jeans or longer skirts.

How to wear colored tights?

Keep the rest of the outfit in one color and then accentuate your fabulous legs in a different color. Of course this look would only be suitable if you like to highlight your legs. Do the opposite if you like to downplay your legs. You can also wear the same color tights as your skirt. I offer some more tips and lots of examples in my article: how to wear tights.

How to wear capris in the winter?

I would wear them with some fabulous booties! If you want to be extra playful you can combine those booties with some printed socks.

How to wear a long sweater at 40?

If the sweater is really long it will be great to wear with skinnies or leggings. In that case it would need to be longer than the hips though. It can also look fab over a straight skirt.

How to style women with no shape?

I believe every woman has a shape! But if you are referring to someone with a rectangle shape, I offer some tips here. Or check my general body shape guidelines.

How to make old ladies look hip?

I think ‘old ladies’ can dress exactly the same way as women in their 40s so all the guidelines on this site will apply. It’s a combinations of the right attitude, right clothes, the hippest shoes you can still manage to walk in, accessories and a focus on health. For the ultimate inspiration be sure to check out these ladies from Fabulous Fashionistas!

Do you agree with my answers to these questions or do you have some other ideas?


{ 19 comments… read them below or add one }

1 33

another great entry! you really thought long and hard on these questions because your answers are right on. I concur with every point you made.

i think women who enjoy dressing to maximize joy and beauty will always do so until their mind and body can no longer support the endeavor.


2 Sylvia

Yes I think so too. I know that we have to compromise on some things sooner or later (for most women it’s shoes) but rather later than sooner I hope!


3 Patti @ NotDeadYet Style

great post! I agree that the “hippest” shoes one can manage are a great way to look youthful but not silly : >


4 Sylvia

That is the great thing about shoes. You can do anything you like!


5 Rebecca

Great post. Some wonderful and positive ways of being stylish after 40. I especially love the answer to the last question. And the comment by 33 is right on!


6 Sylvia

Thanks Rebecca!


7 Greetje Kamminga

I agree with everything. A bit of a boring comment but I cannot add anything.


8 Sylvia



9 Annette

I agree, Sylvia and recently did a post on the various types of shapewear which is an essential part when I wear body con dresses or pencil skirts.
You are right about the length of skirts, most of the time a bit longer is better and when I am in doubt, opaque tights allow me to go a few centimeters shorter.
Shoes are a key element and can completely ruin or enhance a look. Therefore I find them most important.
This weekend I am looking for an oversized sweater which I want to wear with my pencil skirts!

Annette | Lady of Style


10 Sylvia

Hope you find something nice Annette. Have fun shopping!


11 Suzanne

I always think you have the best answers to our questions. 🙂 Unlike so many other stylists, you have the ability to recommend what is flattering for an individual and not impose your own choices on them. That is a talent – one that makes your blog successful. We all need to dress to fit our own bodies, taste, and lifestyle. I am finding that it is the ever changing circumstances of life that has the most influence on my wardrobe. What I wore as a young mother is no longer how I dress as a college mom. Someday I will no longer be that and life will change again. You need to keep an open mind and keep growing. Stay engaged – in fashion, the arts, current events – whatever interests you. Learn new things! Women who are charming (who allow their inner joy to shine) remain attractive their entire lives. Thank you for letting us shine here Sylvia!


12 catherine

Great post and right on Sylvia
I love these fabulous fashionistas, really out of the box these ladies


13 Sylvia

Thanks Catherine. They are a true inspiration to me!


14 Judy

Where can your readers purchase clothing items you show on your web? I really like the light grey sweater with the classy drape shawl collar suggested in Classy, Casual Holiday season. Please advise.
Thank you


15 Sylvia

I usually provide links to any clothes that I feature. However, since it’s fashion, items quickly get sold out. So if you don’t see any links or product items below the article, it means that the article is no longer available.


16 Jenniferk

I found this site while looking for answers on whether a 42 year old woman could wear a jumpsuit/romper. I’ve seen quite a few magazines with this trend but I’m just not sure if it is appropriate over 40?


17 Sylvia

Hi Jennifer. It really all depends on how you style it. You can check some great examples at The Lady of Style who is doing a styling series on a jumpsuit at the moment


18 Aileen

These are all great tips to follow, as are the other ideas and suggestions throughout your website, Sylvia.


19 Natalie

Thanks for the tips Sylvia. My biggest fear as a now 60 year old (when did that happen!!) is that dressing on trend will appear desperate. Thank you for highlighting women who are well past 40 and rocking the trends in a chic and inspiring way.


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