I am a big fan of shorts. I’ll happily throw on a pair when it’s scorching hot in the middle of summer, preferably after applying a good amount of self-tanner on my pasty white legs to boost my confidence and hide my veins.

When styled well, shorts are a fashionable way to stay cool and comfortable in warm weather. 

But I know from experience that not everyone is comfortable wearing shorts, especially as we get older and that they can be hard to style.

So, today I want to share some tips on how to wear shorts for women over 40.

How to Wear Shorts Over 40: Tips and Outfits 

Why do I say “over 40” when I also think age has nothing to do with what you “should” wear?

Mostly because I’m the mom of three girls, two of which are teenagers and the way THEY wear shorts is not going to work for me at 44. They can throw on short little shorts and even shorter little tops and look adorable.

And, listen, if you’re comfortable wearing that, more power to you.

But after three babies and my style getting more sophisticated over time, it’s not for me.

When it comes to style tips for women over 40, I often stress the importance of comfort. 

More specifically, the importance of wearing clothes you feel comfortable and confident in.

And you can feel comfortable and confident without compromising style.

The first and most important step in feeling great in shorts is to find a fit and style that works for you. Personally, my favorite shorts come mostly from J.Crew, and a few from Gap/Gap Factory. But throughout the site we’ve featured all different options from stores and brands like Ann Taylor, Talbots, Spanx and Amazon.

It doesn’t matter where you buy them, but you want to pay attention to the what rise and inseam work best for your body type.

Then, you can begin coordinating outfits to wear with them. 

And if shorts just aren’t your thing, check out my post on what to wear when you don’t wear shorts!

Shorts Outfits for Over 40

Long-Sleeve Striped Top With Chino Shorts

I featured this outfit in my post Great Shorts for Women Over 40.

It’s the perfect summer outfit if you don’t like showing your arms. The top is a lightweight knit that covers your arms, but zhuzh them up at your elbow to help style the look.

I paired them with 4″ shorts have a nice amount of stretch from J.Crew. I’m 5’10 and wear between a 4″ – 5″ inseam comfortably.

And I ground the look with our favorite slides from Tuckernuck and the Lo & Sons crossbody bag The Pearl.

Trouser Shorts With Blazer

I recently discovered these cotton shorts from Amazon, for only $15 and they are lovely. They are cut like a trouser with a little bit of elastic at the back. They come with a belt but I swapped it out for a different one. Featured is a new leather belt I found on Amazon, with your choice of leather and metal color for $19.99.

Then, I found The Diana Blazer on Tuckernuck (named after Princess Diana) and it’s stunning. A worth-the-splurge buy now wear now and later find.

You can see how gorgeous it is on the model here.

Obviously you’re not wearing a blazer with shorts in 100 degree heat, but if it’s mild out or you’ll be in air conditioning, it’s a wonderful way to add structure and elevate the look.

The way this blazer fits is important when paired with shorts. You don’t want one that hits at your waist, rather, let this hit around where your fingertips hit your leg – a little on the long side.

I’d wear this touring someplace fabulous, with this white Everlane tee underneath and chic navy and white sneakers from Veja.

Round out the look with your favorite gold-tone jewelry to go back to the gold buttons of the blazer.

Chambray Shorts With an Eyelet Top

One of the challenges with short outfits is that your pieces are limited. In the heat you don’t want to wear a lot of layers, so you have to use other elements to add interest.

That’s were texture comes in. Working with simple pieces that have lots of texture gives you visual interest when you don’t have layers.

So these 5-inch Classic Chambray Short from J.Crew Factory are a great option.

I paired them with this breezy eyelet top from Nordstrom, and this popular pair of braided white sandals from Rothy’s.

Don’t forget accessories. These Julie Vos pearl earrings have been a longtime reader fave, and add a bit of sophistication.

Pop of Red with a Polo

Shorts are a great opportunity to play with color and pattern. And if you don’t have a red pair already, they would be the first on my shopping list after your neutrals are covered. * I recently bought a pair of Kelly green shorts and they are also wonderfully versatile.

Featured is a linen blend with a 4″ inseam from J.Crew.

I paired with a slim polo from Gap.

I find polos to be a great wardrobe addition because they wear like a simple tee but the collar and fit elevate the outfit.

Then, to add interest, a woven belt and raffia sandals.

And shout-out to these $14 Amazon earrings that were on our best sellers list from Prime week. If you have them, wear them with anything!

Denim Shorts With A Graphic Tee

I recently dedicated a post to Graphic Tees for Women because they’re perfect for adding styling, comfort, and personality to an outfit.

They also look great with denim shorts. 

This fun Fleetwood Mac Graphic Tee was a best-seller from my post on my favorite finds from EVEREVE.

Paired with light-wash jean shorts and white sneakers for a casual, everyday outfit.

Add a neutral belt bag and have a sporty look for outdoor festivals or concerts.

Bermuda Shorts With an V-Neck Top

Finally, if you want a longer length, consider a Bermuda short, but use some caution.

These can get real frumpy real fast.

Keep a few things in mind. You want the leg of the shorts to fall away from your body, the ones that tapper in are not flattering on anyone.

Next, pay close attention to your best inseam, which will vary based on your height. You want these to stop about 2″ above your knee.

I like this 10″ inseam from, you guessed it, J.Crew. They have the best size selection and price point out there.

When styling look for a top with a scoop or v neck to help elongate the line of the body. Here I’m using this sleeveless ruffle top from Vince Camuto. The ruffle also adds interest without adding layers or bulk.

Finally, I’m using this pair of Jack Rogers sandals to add a little glam and texture.

What’s your favorite way to wear shorts?

Whether you prefer short shorts or Bermuda-length bottoms, shorts are a must-have for hot summer days.

Find a pair you feel comfortable and confident in, then you can mix and match it with various pieces to create stylish looks all summer long!
For more outfit ideas and style inspiration, head over to the blog!