Fun or Foolish? 7 Tips for Dressing your Age When You Are Over 40
Recently, we wrote a blog post called What NOT to Wear After 40…and put up a photo of these shoes.

We were surprised to get several emails from gals who loved these wild shoes and had no problem wearing them regardless of age. This got us thinking…. where does one draw the line when trying to decide what is fun to wear and what is foolish to wear after 40?
Our take on these shoes is that while they are fun and new, they are definitely loud and may look foolish, not fun, on most women over 40. Although the style is fashion forward and the high heel does have a hidden platform, which makes it doable, the kicker for us is the hot purple color combined with shiny patent leather, which makes it too trendy for most. The wide strap also adds a baby doll feel.
But all that being said, if you have a big dramatic or creative streak in you, you might be able to pull off these shoes, if you wore them with a simple outfit like a sleek black top and pair of black wide legged pants. Make these shoes your statement piece and don’t junk up your look by adding all kinds of other trendy bits like, i.e. an animal print belt with these shoes would send your image into a fashion tailspin.
We mentioned you really have to have a certain drama to your coloring as well to pull this look off. For example, if you have a fair skin tone and very dark hair and eyes, or dark skin, and a dramatic aura, this might work. If you are blonde and light skinned, these shoes won’t fly because the contrast is so great, they’ll make you look cheap.
For those a little less bold, you may want to try shoe in black patent leather, instead of purple, or you might also want to look for a less bright shade of purple shoe in suede or leather. Choose one without the ankle strap if you want to look as tall as you can.
Curious about where we draw the line between fun and foolish when it comes to 6 other new fall looks. Read On……
1. Extra Wide Legged Pants
![]() Fun or Foolish? |
Our Pick |
You could mop the floor in the pants on the left. We don’t want to take the fun out of fashion but these pants are on the extreme side.
Our Pick
These high-waisted Diane von Furstenberg pants are a better choice because they have a more gentle flare which is very flattering on most body types and balances out any over 40 body which is usually starting to widen through the middle. The hot pink window pane pattern adds a touch of femininity to the men’s wear feel.
2. Bright Bold Prints
Layering and bold prints are in, but the combination of the two on the left looks busy and tacky. This look is too playful for a 40+ look unless you are Carrie Bradshaw, (but isn’t she starting to look a little silly in some of her zany looks anyhow?)
![]() Fun or Foolish? |
Our Pick |
Can you believe this is the same dress? What an improvement! Leave a busy patterned dress alone by dumping the vest and belt. Much more beautiful and age flattering!
Our Pick Too! |
Here’s another bright, bold Diane Von Furstenberg dress. It’s called “The Clooney”. Again, if you are going for patterns stick to classic style that is simple and let the pattern shine. This knock-out number has a geometric pattern with an art deco feel, which is a hot trend this fall. |
3. Short Sleeved Suits
Fun or Foolish? |
Our Pick |
JoJami saw this Nanette Lepore suit (on the left) at a local boutique, but didn’t have time to try it on and was thinking of going back to do so. But when she saw it here she realized it has a lot of problems. It has too much going on. This jacket is trying too hard to be different and the lace top is an added extra that’s just not needed. On an over 40 gal it would look plain granny like.
Our Pick
We prefer this Isabel and Nina double breasted wide shawl collar suit. It’s got a real Jackie-O quality to it – sophisticated and clean – and the neckline is so elegant.
4. Wild Animal Prints
Fun or Foolish? |
Our Pick |
Animal prints are fun but don’t have to roar so loud that you look like you are wearing a costume. The zebra inspired skirt on the left is cutesy if you are twenty but, cutesy is not the way you want to look.
Our Pick
We vote for the look on the right. Simply add a touch of animal print to an accessory like a handbag or belt and you look so much more sophisticated. It’s the difference between fashion Victim and fashion Victory!
5. Fashionably Full Skirts
Fun or Foolish? |
Our Pick |
The combination of this ruffled blouse with puff sleeves and very full pleated skirt makes this young model look a little older than she is, and that’s fine because she is so young to begin with. But put a prissy school teacher look like this on a gal 40+ who has extra curves at her middle, not so perfectly taught arms, and a mature face and she’ll look like an old biddy.
Our Pick
If you like a fuller skirt, try one that is a little more refined. This Ralph Lauren box pleated wool herringbone skirt is easy and comfortable to wear and always looks classy. Top it off with something more relaxed like a black turtleneck and great suede jacket in a gorgeous shade of majestic purple. This shot of color will give your face life.
6. Chunky Platform Shoes
Fun or Foolish? |
Our Pick |
Clunky and funky, these top heavy shoes (on the left) with their baby doll strap would look better on your teenage daughter.
Elegant, classic with a modern twist these Tory Burch Pumps look great and the stacked heel makes them a lot more comfortable for tootsies too. Love the gold hardware!






Fun or Foolish?
Our Pick
Fun or Foolish?
Our Pick
Fun or Foolish?
Our Pick






I agree with your picks. And about the shoes, yes, although fun, the problem with women TYPICALLY over 40 wearing shoes like that do tend to junk it up with the other things too and just end up looking like they are trying too hard to be 20.
Nice job on the “what older women should wear” topic. It’s terrific to have photos to illustrate your points.
I’ve seen lots of blogs and Web sites that are writing about this topic. Older women seem to be really concerned about it. I’ve even written about it myself several times.
A couple of recommendations that you didn’t follow from the standard list: older women shouldn’t wear black, plunging necklines, short sleeves, or bold colors.
Rita
Hi I am 21 and I was wondering if you could tell me the brand or where I can buy the purple heels at I love them!!!
Are you familiar with Betsy Johnson. My 12 year old LOVES her dresses. Unfortunately, so does Ms. Johnson, who must be in her late 60s/early 70s… It’s horrible. She could really use some of your advice… Something like, your dresses are gorgeous for young girls. However, not so much for the over 40s crowd.
Thanks for all of your advice.
Hi Gwenn,
Betsy Johnson is one of those women who get to not only look forever young but dress forever young!! She is just having fun promoting her line of dresses and we love her. However you are right in stating that her dresses are ment for younger gals. We think she gets to be an exception to the rule, since she is just a walking postcard for her brand.
Greetings! Just curious as to why you don’t use models over 40. I would think it inspiring and also that it would better illustrate how the looks work well on these women.
I agree with the 7 and of course we can always add more! How about jeans – I’ve seen styles on women over 40 that are totally inappropriate – either too old or too young – no one looks good with a “muffin top” no matter what your age. Women trying to wear their daughters clothes need to stop! I would also suggest that there is a level of comfort that women over 40 are looking for – whether it be in shoes or clothes – this can also be achieved by choosing/buying correctly – i.e. Dansko clogs are comfortable and stylish, Eileen Fisher makes beautiful clothes that aren’t form fitting, but flowly and comfortable, yet stylish. You can actually look young if things fit, are age/body shape/season appropriate and match your color pallette.
I’m glad you didn’t quote the “standard list” in your article. In my 50s, I often wear black, and bold colors on occasion. I hope this is not considered taboo! Thank you for the helpful article.
It’s great to have guidelines and common sense when it comes to dressing after 40. However, you can’t pigeonhole people into one way of dressing. We all have different personalities, lifestyles, and professions. Not to mention different coloring, shapes, and sizes. It’s a matter of finding what works best and looks best on each of us individually, given the previously metioned factors. Betsy Johnson looks amazing for who she is and what she does. She is true to herself and isn’t trying to be something she’s not. I’m also artistic and work in a very creative field, and have more freedom than someone in a conservative corporate job, or the typical soccer mom. So I tend to be more daring and dramatic in my choices. I have purple shoes, however, they are a red-purple suede wedge loafer with a flower on top. Be comfortable, be you, and have fun!
I think we’re blazing a new trail with what is appropriate for “older” women. Each woman has to honestly assess herself to determine what looks good. At 40 I looked more like early 30′s and any of those “fun or foolish” looks would have worked for me. Now in my early 50′s I have to be a bit more careful, don’t want to look like mutton dressed as lamb, but I will always dress with a youthful exuberance, it just suits my personality.
As always, excellent suggestions Glam Gals! I prefer to call my clients over 40 “experienced, mature, or established” not “older”. After 40, I certainly don’t feel old. However, we must be aware our bodies are changing as we age. It is a good idea to change our wardrobe to accommodate those changes and still look our best. This doesn’t mean we can’t still have some fun w/ our wardrobe choices. Thank you for illustrating that well Glam Gals.
Appreciate all you share,
Lori Johnson
Your Best Image, Professional Image Development.
Hi Lori,
Yes, we try to use all different types of words to refer to us, over 40 Gals…but the bottom line is, what is a number anyway??? We are writing this blog to inspire women to have fun with dressing no matter what their age! But dressing age appropriate can be a challenge too…. so The Glam Gals are here to try to give our advice on striking a nice balance!
age is just a number. people should dress in what is appropriate for them.