How to Create Casual, Classy Shorts Outfits Over 40, 50

You may have hung up your daisy duke years ago (which is a good thing-lol!), but that doesn’t mean you can’t wear shorts at any age. It’s easy to rock shorts at midlife and beyond when you tweak your chic! Here’s how to style classy, casual shorts outfits over 40,50 and more.


long-shorts rust

I like shorts; they have their time and place, and I’m not ready to give them up anytime soon. But I wear them a little differently at 50+ than I would have years ago. In my 20, 30, and even early 40, I could throw on a fun pair of colorful short shorts with just about any old tee, and I looked cute.  Now, I just look frumpy. Instead, I prefer to look more pulled together in casual shorts outfits with a slightly elegant vibe.

long-rust shorts

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How do I achieve that?




1. Wear Longer ( but not boring) Shorts

Even though my legs are still toned, short shorts feel too junior to me. On the other hand, Bermuda shorts can feel a little stodgy if that’s my only choice. Sometimes I like wearing a perkier pair of shorts, like at the beach.  I’ve experimented and found that I’m good with an inseam of at least 5 -9 inches or even 11. (Anything shorter looks like I wish I were 18! )

I suggest you order a bunch of shorts and try them on to see what looks and feels right for you.  You will know once you take a look in your full-length mirror. I can guarantee that! (Lol!) Crisper, more tailored shorts look more polished than looser, flowy shorts. Cuffed shorts are trending and add style and sophistication.

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2. Be Thoughtful about Choosing a Top

The next step is choosing a top. You need to be thoughtful about this to create a fabulous outfit. What look are you going for? Tees are fine when they are neat and more fitted to your curves. This gives you a very polished, sporty look.  I like feminine and silky tops to elevate a shorts look, for example, in the first photo of me in the rust shorts.

I could have easily worn that with a tee, but it would have looked quite plain. Instead, I found this long, silky top at Amazon with the lace-trimmed neckline that has a modern leopard print mixed with a few subtle florals. It’s soft and flowy, and I can wear it tucked out for a relaxed, elegant look. The fabric alone makes it look much more expensive than a basic tee.

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shorts - white



Many women find they want sleeves after 50, and that’s fine; leg-baring shorts worn with a top with sleeves will make you look elegant. For example, you could wear white shorts with a beautiful long-sleeved peasant blouse. Full details are important too. They also set the mood for your outfit. For instance, a pretty top with a small ruffle at the neckline makes your outfit look more romantic and feminine.

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3. Fabulous Accessories are a Must

Accessories are the secret sauce to pulling together all the elements and creating a classy shorts look. Modern, sophisticated accessories elevate shorts and make them look more chic than fun. Pay attention to your shoes. Say no to flip flops and try mules, statement sneakers, slides, wedges, espadrilles – anything more interesting.

Add a classy bag and a belt in some cases. A touch of jewelry ( too much looks tacky) is a must when styling an elegant shorts outfit. And of course, a fantastic pair of sunnies are the icing on the cake.

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So there is your style recipe for a casual summer shorts outfit for over 40,50, and beyond.

  • Wear longer but not boring shorts
  • Be thoughtful about choosing a modern top
  • Fabulous Accessories tie it all together to create a look

Keep it classy, not kooky or too cutesie. and you will rock those shorts at any age!

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One thought on “How to Create Casual, Classy Shorts Outfits Over 40, 50

  1. My legs are still my best feature, even though I’m a few months shy of 70. I would never give up shorts. However, one can’t stop the inevitable crinkling of the inner thighs. I have lengthened the shorts. A Bermuda length is my best friend, and I have an entire collection of colors.

xo, Deb

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