How To Style The Bermuda Jean Shorts Trend When You’re Over 40

One of the stand-out trends on the runways for Spring 2019 was Bermuda shorts and we recommended them for women over 40. However, we also did warn that fitting and styling them would be a little tricky. After all you don’t want to look dowdy or like you are trapped in the 80s! But in their spring 2019 collections designers showed us some new ways to style shorts to the knee. One of my personal favorites was the shorts suit. This look was so sophisticated and a modern change from the jacket and skirt. Recently I noticed many options for slim jean shorts to the knee, and they look fantastic when paired with an oversized boyfriend jacket. This look is much more wearable than a full-on matching suit, and you can get this look by spending a little or a lot. Here’s how to style the Bermuda jean shorts trend high or low.

How to Wear Knee Length Denim Shorts When You’re Over 40

1. First of all, get the best fit. To find the best pair of shorts for you, consider the skirt length that flatters you most. I was excited about the knee length denim shorts that hit the middle of the knee, because that is a good skirt length for me. You may need to go a little shorter or longer, and you can get them more fitted like bike shorts to show off your legs, or slightly loser. For most women, looser is better, but still keep the shorts sleek and close to the body.

2. Make your own knee length denim shorts! Cut a pair of your straight leg or skinny jeans to the length that works for you for a custom look. Put the jeans on and measure them against a skirt you like. Then mark the length carefully with the jeans on you body. You can also roll them up to get an idea of how they will look as shorts. Remember, always cut the legs a 1/2” longer, because you can always cut more but never add back.


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3. Get the right proportions. Wear a long blazer over it (like my outfit above). An oversized boyfriend jacket that covers your hips will balance out the look. You’ll also feel more comfortable wearing something roomy with the slim line shorts.

4. Keep your shoes on the lighter side. Don’t wear chunky or heavy shoes that will shorten your legs, rather elongate your legs by wearing as bare of a shoe as possible. The new way to wear knee length denim shorts is with open strappy slides, either with a low stiletto heel or flats. Think about wearing the same types of shoes you would with a pencil skirt when you wear long shorts!

5. Have fun with the contrast of dressed-up and dressed-down when styling long denim shorts. Wear a casual cotton tee with distressed jean shorts to  contrast the dressed-up menswear jacket and strappy sandals. This play on dressy vs. casual is what makes the look work.

Shop The Boyfriend Jacket and Bermuda Jean Shorts Look 

Now let’s shop! Shop the high end look (pictured above on the left) or the low priced look (on the right) or mix up the pieces for high-low styling.

High Priced Look = $2,703

AGOLDE Carrie Denim Shorts, $138

Acne Studios Double-breasted Grain de Poudre Blazer, $700

RAG & BONE Ramona Scoop Neck Tee, $125

Cushnie Brown Leather Bucket Bag, $1,095

MANOLO BLAHNIK Iacopo Double Band Sandal, $645


Low Priced Look = $336.94

H&M Knee-length Denim Shorts, $34.99

Caslon Linen Blend Boyfriend Blazer, $69

Caslon Rounded V-Neck Tee, $25

Madewell The Austin Crossbody Bag, $128

NINE WEST Lynton Sandal, 79.95

Will you be wearing the denim Bermuda shorts trend this season? How will you style them? And will you go high or low?

Carol Calacci

You may also like to read Steal Her Style! Get This Gabrielle Union Leopard Dress Look for Less and How To Get This Julianne Moore Bold Monochromatic Look For Less.

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How to Wear Knee Length Denim Shorts

2 thoughts on “How To Style The Bermuda Jean Shorts Trend When You’re Over 40”

  1. Thanks for sharing this. Perfect timing! I just bought a few pairs of Bermuda shorts, tried them on and could not figure out what to wear with them. Loved your ideas!


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