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?
wideleg-pants-smOur 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?
bold-dots-smOur 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!

clooney-dressOur 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

foolish-suitFun or Foolish? doublebreast-suit-smOur 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

animal-print-skirtFun or Foolish? animal-print-purseOur 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?

ralph-lauren-lgOur 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

foolish-pumpsFun or Foolish? suede-pumps-lgOur 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!

Cindy McCain, looking totally glamorous!

First, Michelle Obama, now its Cindy McCain.

We are just amazed how these woman are putting Glam back in politics!

We have been watching them and they just  keep looking better and better.

Look at this…out with the old, in with the new.

Mc_and_bush_2This picture is just classic! Here, Laura Bush is in her old fuddy duddy knit suit and then just look at that gorgeous dress McCain has on!!! We love the color on her (not an easy color for most people to pull off) and the way she has accessories it with jewelry, no belt. Once again, simple elegance.

What can we learn from this?

We know we all have things in our closet that we pull out at certain times, just to get one more wear out of it. Please run to your closets and get rid of those old things! Don’t keep them in there, thinking, I just might need to wear it one day…

We have heard from so many of you that you, that you want to feel more youthful, and look more youthful. Well the easiest way to do that is to stop wearing your old out of date things!

Come on, its going to be a fun ride!

Michelle Obama Style! How Does She Do It?

Most women in politics (on both sides) feel the need to show a very conservative and boring style of dressing, however, Michelle Obama has shaken things up and is dressing the way we feel a woman over 40 should. She’s raised the bar on style after 40!

Lets take a look at some recent photo’s and analyze what she is doing right!

Mo_looking_glamours_in_pink_2Here she is radiant and glowing in a lovely, soft flowing pink floral gown.She has a lovely tone and graceful upper body and she is showing it off just perfectly without looking too sexy.

Mo_on_the_view_2 <When Ms. Obama appeared on, The View, sales of this White House, Black Market dress went off the charts! She certainly found a way to stand out in the middle of some pretty powerful women!
Mo_purple_dress_2 < Here she is a a figure flattering purple Jackie O inspired dress. Look how she has added a simple belt (one that is not matchy matchy) and oversized pearls to accesssorize. The belt reminds us of the one Carrie wore with her shift dress in the recent Sex and the City movie.Her hairstyle is cut in an attractive and updated style and she always has on just enough make up to keep her looking pulled together.


We realize that not all of us are almost 6′ tall and slim, however, we can take inspiration from her classic style to look great!