A Dressy Shorts Outfit that Looks Amazing at 50+

I’ve always enjoyed wearing shorts in summer, but, like most women, when I reached midlife, I found myself starting to wear them less and less. I began feeling a little self-conscious about my pale legs, spider veins, and loose skin, so shorts disappeared out of my wardrobe.

But I’m over all that now. I’ve had my spider veins treated,  discovered some excellent self-tanner, and I don’t care about loose skin. I’ve started exploring new ways to wear shorts that look classy and modern, and I’ve had some luck.


Last spring, I styled a classic pair of Bermuda shorts with a bright jacket, and the post was a big hit. Today I want to show you another shorts outfit that may get you rethinking this whole shorts thing, too.


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This is my new favorite summer find! It’s a chic shorts suit from Karen Kane. I think it makes a lot of sense because when you want to look classy and polished, you wear a suit, so why not the same when you wear shorts? This smart-looking suit is made of 100%  linen, so it’s not stiff or formal even though it looks tailored. It does wrinkle, but that’s what makes it charming and gives it that laid-back vibe so fresh and modern.

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I like the length of these breezy shorts. They hit a mid-thigh, so they are not too short ( I have long legs), but not too long. I know this length will appeal to some and not others, but overall I think it is a perky yet classy length.

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These shorts are also high-waisted, which is quite flattering and makes them look more formal like trousers. But they’re also very comfy since they have an elasticized waistband! The slanted pockets give them that classic suit feels. I thought this buttery soft tank was the perfect top for a suit like this. You need a top that is light and casual to keep the look relaxed but chic.

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I chose this beautiful blue color, but this outfit also comes in a lovely soft gray. The jacket is light and a little fitted, and the elbow-length sleeves are ruched, so you don’t have to keep pushing them up to get that sporty scrunched-up effect! I love those big patch pockets too!



My inspiration for the accessories came from the gorgeous Cherry Blossoms here at Spencer Smith Park in Burlington. I added a pale pink bag and these pinky, nude mules. I love the way it contrasts with the navy and softens the masculine suiting.

My gorgeous gold initial necklace, bangle bracelet, gemstone bracelet, and double drop earrings from Dean Davidson also add a touch of class!

And that’s my new summer shorts look! To shop this outfit, click the links in this post or be sure to visit Karen Kane for this and other fabulous summer finds!

Still undecided about wearing shorts? Check out my post on how to confidently wear shorts at 40, 50, 60 and beyond.

*Thanks to Karen Kane for partnering on this post. All opinions are mine.



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xo, Deb

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