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.

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

How do I achieve that?

long-rust shorts

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.

white shorts blue top

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.


black shorts pink sweater

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!

Visited 10,947 times, 3 visit(s) today
Join the Conversation

4 thoughts on “How to Style Classy Shorts Outfits to Look Fab Over 40, 50

  1. Thanks for the great suggestions. I especially love the combination of black shorts and a pink cardigan. The sandals are a great addition!

    1. Thanks, Connie, You could easily wear this outfit with black sandals, but I like the pattern and texture of the snake print and the way it takes a classic looking outfit and adds a touch of wildness! Modern!

  2. I have been going Healthplex working on strength training since I’m petite and I have the bone density thing. One great thing is that all the mat exercises we do at the end of class have strengthened my legs, abs, and core and the machines I do also work on the inner and outer thigh area. I was excited to get back into shorts with self-tanner, and my Derma Blend body cover stick for bruises or veins. Like you, I chose a elevated white blouse that was cool and had an open weave just around the upper neck area. It also has a small ruffle edge at the neckline and I wear it with a pair of fringed casual, white jean shorts I cut from Bermuda length. I added white sandals and white and gold earrings. I got lots of compliments on it at church brunch yesterday and stayed cool in this heat wave in the Southern States. Thanks for all the tips because my petite legs can’t do Bermuda length at all, and I had to decide on a length to buy and had already bought 3 pairs of white denim Bermudas I didn’t wear. Banana Republic had some nice ones I bought. I will check out your places here too.

  3. 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.

It's your life. Make it Fabulous!

This error message is only visible to WordPress admins
There has been a problem with your Instagram Feed.