Stylish Shorts Outfits for Over 40, 50

Dear Deborah,

I’m 46 and have wrestled with whether I can still wear shorts for far too long, so I’ve decided to just go for it! The problem is, I haven’t bought shorts in ages, and I’m not sure what’s in? Can you give me a few ideas for stylish shorts outfits that work over 40? Thanks, Sharon

Hi Sharon,

I’m so glad to hear you’ve decided to embrace shorts. So many women wonder if shorts are age appropriate, when in fact they are. To look great in shorts at any age, all you need to do is find a pair that 1) suits your body type and  2) is currently in fashion. Then, combine them the latest tops, shoes and (don’t forget) accessories to create modern looking shorts outfits. Here are a few examples of popular types of shorts and how to style them into outfits.

Paperbag Shorts

If you follow my blog, you know I wrote a whole post about the front tie trend. Front tie pants are everywhere, and now we’re seeing front tie shorts too. This is a super popular look and a great starting point for a cute shorts outfit. These floral shorts are very pretty and ladylike and to make them look great, just add a relaxed sleeveless summer top in white or a color from the print.

Slides or flat sandals go with it, or you can dress these shorts up a touch with a low heel sandal like this one above. It’s the cute accessories that really elevate this outfit. Beaded tassel earrings are fun and modern to pair with casual shorts. The purple crossbody bag is sporty and ties the whole look together.

Bermuda Shorts 

You’ve asked, and I’m now reporting that Bermuda shorts are back. They’ve always been around but were kind of lurking in the background. This summer they’ve returned in full force. Women appreciate the fuller coverage and brands have come up with new ways to style them that shifts them from frumpy to fabulous territory.

These hot pink Bermuda shorts have built-in stretch which gives them a super comfortable fit and sleek look. Wear them with a longer top and a cute pair of slides for a sophisticated summer look.

Gingham Shorts 

Gingham is another fashion trend that has been very popular and is a natural choice for shorts. Pink or baby blue denim can look a little sappy over 40, but these black and white gingham shorts make up for that. These are cute without being too cute. Black and white always looks sophisticated even when you have a casual summer look like this.

This breezy bell sleeve top is a nice complement to these crisp shorts, and the black slides and tassel crossbody make this shorts outfit look classy and cool.

Cargo Shorts 

There are some shorts we never get tired of which is why cargo shorts are still so popular. When you want to create an adventurous, active summer look, these shorts are a perfect choice. Top off a pair of khaki utility shorts like these with a simple cotton tee in a bright color to add some punch.

This tee has a lovely ruffle which adds a touch of femininity to a more masculine short. Metallic slip-on espadrilles and a studded tote give it some glam.

So there you go Sharon, four styles of shorts that are trending right now to create stylish shorts outfits at 40+ or any age!

Short Shorts

Short colorful shorts are always in style, and if you have the legs for it, for it! This cute outfit looks smart because it appears well thought out. Everything coordinates, the sandals are cute and we’ve added jewelry and a jacket to make it look a little more polished than just wearing it with flip-flops and a plain tee.

Want more ideas for wearing shorts? Here’s the full story on how to wear shorts at our age.

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