How to Style Classy Shorts Outfits to Look Fab 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.

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 look frumpy. Instead, I prefer to look more pulled together in short casual outfits with a slightly elegant vibe.

How do I achieve that?

shorts | top | sandals | clutch bag

1.Be thoughtful about Choosing a Top

I like a  feminine, silky top like this one to elevate the look of shorts.

I could have easily worn these shorts with a plain-colored tee, but it would have looked quite plain. Instead, I found this long, silky top at Amazon with the lace-trimmed neckline with a modern leopard print mixed with a few subtle florals.

It’s soft,  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.

shorts | top | denim jacket | sunglasses | straw bag

2. 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 frumpy 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.

top | shorts

3. Go Monochromatic

An easy way to make shorts look dressier is to style your outfit monochromatically. In other words, tone-on-tone shades of one color. Shades of black are always chic and look chic when paired. This cute black print-sleeve tee is one of my favorites. It is relaxed and comfy, but the gathered neckline and cape sleeves make it unique and modern.

pink cardigan | white tank | black shorts | belt | monogram bag | sandals |earrings

4. Add a Third Piece, like a Cardigan

I often mentioned how something as simple as a third piece in an outfit can elevate a look. That’s the case with this gorgeous pink cardigan that adds a dash of formality to casual shorts. Do you recognize the tank top with the lace trim? It’s the same as the animal print one I showed at the start. You can’t go wrong with a versatile piece like this. A nice belt and some jewelry also add to the smart look.

green top | black shorts | monogram bag

5. 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.

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

• Be thoughtful choosing a modern top
• Wear longer but not boring shorts
• Go monochromatic
• Add a 3rd piece, like a cardigan
• Fabulous Accessories tie it all together to create a look

Keep it classy, not kooky or too cutsey to rock those shorts at any age!