Is Age Appropriate Dressing All In Your Head?

Of all the questions my readers send me, the one I seem to get the most is a variation on the theme of age-appropriate dressing: “Can I wear short skirts/low-cut tops/bikinis/etc. at my age?”;“Does this make me look like I’m trying hard to be young?”; “Does this make me look old?”

I call it the Goldilocks question: “Is this outfit too young, too old, or just right?”

Age appropriate dressing

photo by: Cue Ozop

I recently came across  an  article featuring a series of photos that dramatically demonstrated why dressing “age appropriately” may not be all that it’s cracked up to be. The first half of each of the seven images, by the photographer Cue Qozop, captures parents and their children wearing generationally appropriate clothes; in the second half however, parents and offspring swap outfits. The parents, in essence, are decidedly not dressing age appropriately. And do you know what? They look fantastic!! (Their kids don’t look half-bad either when they are wearing their parents’ clothes, BTW.)
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What Does An Age-Appropriate Leather Jacket Look Like?

orange leather jacketA beautiful leather jacket is an investment that you can enjoy at any age.
The key to looking classy in a leather jacket is to find a jacket that is streamlined and more on the elegant side like this orange one.
The vibe should be mature, urban and chic, rather than rebellious teen at a rock concert if you if you want to look age appropriate.
Here is an example of what I mean…
blue dress with black leather jacket

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Am I Too Old To Wear That?

dressing after 40

How many times have you eyed something cute in the store, picked it up and wondered, "am I too old to wear that"? It's confusing knowing how to dress after 40 because our bodies have changed, our … Continue Reading

Are Patterned Jeans Just for Teens?

floral pants

Hi Deborah, I love the very trendy patterned jeans and wonder if they're too young for the 50+ gals. I found a really cute pair that are wine colored with a tone-on-tone harlequin pattern. They're … Continue Reading

Florals Old Lady – Are You Kidding?

Floral  Trends

You can’t say the words “spring and summer fashion” without mentioning florals. Whether they're the focal point on a dress or splashed all over a pair of pants, florals are a romantic staple of the … Continue Reading

How to Dress Comfortable and Stylish When You’re Over 40 and Beyond


It wouldn't be too outrageous to say that dressing casual is a daily head scratching dilemma.  Between trying to be comfortable and still look classy  and updated  sometimes it just seems easier to … Continue Reading

Poor Fit = Frumpy After 40!

frumpy after 40

We caught you!! Are big baggy sweaters and loose sloppy pants making you look old and frumpy? Go the mirror now. Take a good look. Be honest. Baggy, poorly fitted clothes are a big problem after … Continue Reading

Are These Shoes Age Appropriate?


I got two interesting questions recently asking about shoes that may look too young?. Q. #1 Hi Deb, I was at the mall yesterday and looking for a pair of wedges to wear.  I chose these but now … Continue Reading

Can I Wear A Pleated Skirt After 40?

white sundress

Hi there Deborah, I have seen a lot of pleated skirts for sale lately. I really like them, but was wondering if I can still wear them now I am in my 50's and a little heavier than I was when I wore … Continue Reading

Can You Wear Colored Jeans After 40?

red flare

Hi Deborah! I  love your website and have a question I think most of us are beginning to ask ourselves: Are colored jeans appropriate?  And not just the red ones, I'm talking about the bright … Continue Reading