We’ve recently had a lot of women writing to us to ask us how to wear shorts after 40. Let’s start with what NOT to do:
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Don’t wear baggy cargo shorts. They are better suited to younger gals, and the pockets add extra bulk around your hips and thighs, which we definitely don’t need! |
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Don’t pick a short with pleats. Pleats tend to give you a pooch around your hips, and it’s hard to wear a longer shirt over them without bunching. |
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Don’t choose a style that is too short. Short shorts may be in for the younger set, but at over 40 this look could be very tacky. |
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Don’t choose a style that’s too long. When your shorts hit you below the knee or lower, it will look like you’re wearing capris that shrunk! |
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Don’t buy a short with a cuff around the thigh. This draws attention to the widest part of your leg. |
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Don’t wear a kitten heel or mule with a short. They tend to shorten your leg, and are too formal for this look. |
For an age-appropriate way to wear shorts, try these Dos:
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Do look for a simpler, sleeker line. A straight leg is best, especially when it fitted perfectly to your body. You’ll look taller and thinner! |
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Do pick shorts with a flat front. Most women over 40 look better with a shirt tucked out to camouflage a bulge around the midsection, and flat front shorts is more flattering and less bunchy than pleats under a shirt. |
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Do choose a short right at your, or just above, your knee. Your knee is likely to be the thinnest part of your leg, so you would want to draw the eye there by having your shorts cut off at the knee. |
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Do wear a chunkier heel, wedge, or flat sandal with your shorts. It’s a hipper look and the right formality. |
It’s taken nearly 3 years for us to finally find a decent pair of low rise jeans that don’t create too much of a muffin top when we zip them up. Now the word in the fashion is…
High waisted jeans are the new thing. These jeans come well up over the tummy, right to the bottom of your rib cage. The only saving grace seems to be that they have a nice wide flared leg to balance things out a little and make your waist seem smaller.
It’s a familiar look if you grew up in the 70′s. Remember Charlie’s Angels and every girl who wore flipped up hair and platform shoes? I’ll never forget the pair of high rise blue satin pants I wore to school dances, and JoJami fondly recalls a maroon pair that she used to go disco dancing in.
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Looked great then, but now?? We’ve seen lots of young celebs like Mischa Barton, Kiera Knightly and Jessica Simpson trying them out and they don’t even look so hot.
Some of you may think that high rise will might your hold your stomach in…but only to a point. The problem is that to pull this look off, you have to tuck the shirt in, YIKES! No good for 40+ women with mommy tummies.
We have found that the best way for us gals to wear this look, is to modify it. If you can find a find wide legged pants with a mid high waist, great. Pair them with a form fitting top that can be left out and you will have a great updated look.
If you want to experiment a little with this look, the flat front nautical look is really cute.
Make sure that if you have big hips, that there are no big pockets on front of the pants to draw attention to them. If they do, and you really like the pants, you can also have the pockets taken out.
The wider the flare, the taller you need to be, and you may have to add a big wedge shoe so you don’t look like a short wide traingle.
The bottom line is: THIS STYLE IS HARD TO WEAR, SO BEWARE of this fashion trend!

Sounds like Project Runway’s Tim Gunn assumes that all women over 40 are overweight and out of shape!
His now famous list on Oprah of The Six Things Women over 40 Should Never Wear, might as well have been called, The Six Things Fat Middle Aged Women Should Never Wear!
We totally agree that horizontal stripes, jackets that hit at mid-thigh, pleated pants, double breasted blazers, Capri length pants, and low rise jeans do not flatter heavy or matronly bodies.
But if you’re still looking fit and trim after 40, which many of us are these days, some of these styles will still work.
It’s really more about the shape you are in rather than your age your age. Let your body be your guide.
For example, a pair of cute Capri length pants on a boomer body is a great alternative to shorts. A double breasted jacket can still look classy and fashionable on a slim, mature woman.
A classic horizontal striped top (we’re thinking of the cute navy nautical ones this spring) looks smart and sporty if you’re toned up top and not overly busty.
As for pleated pants, well they look terrible on any woman with a tummy regardless of age, and since flat front pants are what’s in style anyway, why even bother.
Ditto for jackets that fall at mid-thigh.
Low rise jeans, it’s true, are most always best left to young tight bodies, but we think that slightly lower jeans, rather than those frumpy high waisted ones make you look more hip and they flatter most figures.
So go ahead break a few rules. Let your shape, not simply your age, help determine what you should and shouldn’t wear if you want to be stylish at any age.