shorts summer outfits

20 Simple Casual + Classy Chic Shorts Summer Outfits

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Shorts are a summer staple. To be honest, I have a history of feeling very conflicted about them. I don’t love showing my thighs since the texture of my skin has changed with age. Also, thigh dimples are a very real thing. 

But I’m feeling a bit better about them today than I did last summer when I started this blog. I didn’t lose weight or change anything with diet and exercise or start using magic creams or self-tanner. Don’t get me wrong, I’m a fan of considering anything and everything that makes you feel more confident. But the only thing I’ve changed is my clothes.

Somewhere in the process of taking 20,000 outfit pictures, I’ve found a bit more peace with them. Trying new styles of shorts has helped, too.

In this post, I’m wearing one pair of shorts that are shorter than I usually wear. I surprised myself by actually liking them. Pleated shorts have also unexpectedly made their way into my closet. They would normally be a hard pass for me. But I was listening to a webinar on style ruts for my style coach training course and thought, what the heck, doesn’t hurt to try them! So here we are. I love their tailored look.

Today, I have 20 summer shorts outfits for you, with some looks that are super simple casual and some that are classy and chic. Using denim shorts and chinos for casual looks. And pleated linen shorts for the elevated looks. You’ll see pleated shorts showing up everywhere right now as a viable summer fashion choice. 

How to wear shorts over 40

Wear whatever length of shorts you feel confident wearing. For a casual laid-back look, pair them with tank tops, tees, and leather slides or flip-flops. For a tailored look, layer a button-up blouse over a tank top or button it up and tuck it into your shorts. On days you’ll be on your feet and want comfortable shoes and covered arms, wear white sneakers and layer a denim jacket over a tank top with shorts. For a super polished look, choose linen pleated shorts with a white or black blazer. 

For these looks, I’m wearing 3 different pairs of shorts. You’ll see J.Crew Factory white jean shorts, with a 5-inch inseam in my true size, 31. That 5-inch inseam is 3.5-inches when the legs are rolled up. They are 99% cotton with a 12-inch high rise. These feel like short shorts to me, and not surprisingly, they are the pair of shorts my husband likes best. You’ll see me in black Loft Monroe chino shorts. These are the perfect pair of shorts if you don’t want shorts that are too short or too long. They’re a curvy fit with a 6-inch inseam and a 10.5-inch rise. I sized down to a size 10 and usually wear a 12. Lastly, I’m wearing Gap Factory pleated linen shorts in a size 12 with a 14-inch high rise and 5-inch inseam. They have pleats in the front and an elasticized waist in the back.

How to wear casual shorts outfits

There are so many different kinds of tops you can wear with shorts. Try a tank top, t-shirt, a flutter or puff-sleeve shirt, a button-up shirt, sweatshirt, or short sleeve sweater.

Let’s look at summer outfits! 

An olive green tee with denim shorts

If you’re looking for different colors to wear with your bright white shorts, olive green is a stunner. And it happens to be very on trend these days.

An olive green tee with denim shorts

Shorts | Similar Shirt | Similar Shoes | Bag

Add in some brown accessories and the look really pops. 

A gauze dolman shirt with chino shorts

A white dolman sleeve button-up shirt brings an approachable tailored look to a shorts outfit.

A gauze dolman sleeve shirts with chino shorts

Shorts | Similar Top | Bag

Wearing brown leather sandals and a brown leather belt bag adds a richness to this look that I love. These flat sandals are old from Madewell. They were stashed at the bottom of my closet. I’m so glad I didn’t get rid of them. They are on point with this look.

A sweatshirt with denim shorts

A sweatshirt is essential to keep on hand, especially when you’re headed on a beach vacation. When evening breezes put a chill in the air, a sweatshirt is a cozy essential. This is one of the most simple outfits. White denim shorts and white sneakers keep the outfit laid back for casual settings.

A sweatshirt with denim shorts

Shorts | Sweatshirt | Shoes

Swap your shorts out for blue jeans or linen pants if it gets too cold out.

A black tee with denim shorts

A black tee is a staple that you can wear with denim cutoffs or any denim shorts.

A black tee with denim shorts

Shorts | Similar Top

Black and white are always a chic combo, like I’m showing here. 

A striped tank top with denim shorts

I’m all over this green and cream striped tank top. It’s beachy with a pop of unexpected green.

A striped tank top with denim shorts

Shorts | Top | Shoes | Bag

It’s the perfect look for the hot days of summer. 

A pink tee with denim shorts

Here’s a look with a pop of color. Notice the length of my t-shirt. It’s a shorter top that’s longer than a crop top.

A pink tee with denim shorts

Shorts | Tee | Shoes | Bag

It’s the perfect length to wear with high rise jeans and shorts. You can easily just leave it out and it works. 

A boyfriend button down and denim shorts

Here’s a super simple layered look that’s perfect if you’re planning to be poolside but don’t want to wear a bathing suit. Throw a button-down shirt over a ribbed tank top and jean shorts.

A boyfriend button down and denim shorts

Shorts | Top | Bag | Shoes | Button Down

A sweater vest with chino shorts

In summer, you’ll often see knit tops in sweater material. A heavier knit gives a more elevated vibe than a t-shirt. Here I’m wearing a sweater vest that I bought in the winter. Instead of layering it, I’m wearing it alone as a top that’s perfect for hot temperatures. 

A sweater vest with chino shorts

Shorts | Shoes | Bag

A flutter-sleeve blouse with chino shorts

This flutter-sleeve top from J.Crew Factory is one you can dress up with a skirt or dress down with shorts, like I’m wearing here. 

A flutter sleeve blouse with chino shorts

Shorts | Top | Bag

An oversized white button down with workout shorts

A look that Gen Z is loving inspired this outfit. They wear biker shorts and a tank top layered under an oversized button down. I’m doing it with my usual walking workout shorts and a matching tank top.

An oversized white button-down with workout shorts

Button Down | Shoes

I shared this look in my post about alternatives to swimwear. But it’s worth sharing again here. In case you’re curious about other swimsuit alternatives read, 7 Comfy Swimsuit Alternatives That Are Better Than Swimsuits.

A denim jacket with chino shorts

A denim jacket is another summer staple for times when you’ll be in AC. Throw it over a white shirt with black or colored chino shorts.

A denim jacket with chino shorts

Shorts | Shoes | Top | Denim Jacket

Add some white sneakers and you have an easy outfit for running errands or spending your day on your feet.

I wrote an entire blog post devoted to styling these shorts. If you’re looking for more outfit ideas read, 15 Best Black Shorts Outfit Ideas to Copy This Summer.

An oversized white button down and white shorts

An all-white look is simple and always chic. This is another layered look with a classic yet trendy oversized white button down layered over a tank top and white shorts.

An oversized white button-down and white shorts

Shorts | Top | Button Down | Shoes | Bag

I chose raffia slides with a metal buckle for added texture. Plus, a woven beach bag. 

How do you look classy in shorts?

For a classy and chic look, chose an elevated pair of shorts like longer pleated linen shorts. Pair them with a tucked in button-down shirt and elevated sandals and bag. Or wear them with a light short-sleeve sweater. Try layering a blazer over a tank top. Choose platform sandals or slides with extra details, like raffia, or a buckle, for extra visual interest. 

Alright people, it’s time to look at linen khaki pleated shorts outfits! These shorts are great if you want to put together a tailored and elevated look. You can style them so many different ways. Plus, they provide the coverage of a short skirt but in shorts. They’re also super comfortable. I included them in my list of summer wardrobe essentials. See the rest of the essentials in my post, Top Summer 2023 Trends + Casual Summer Outfits Over 40.

A white blazer with pleated khaki shorts

This look is so good! Wear it out to lunch when you want to look put together but also be ready for warm weather.

A white blazer with pleated khaki shorts

Shorts | Shirt | Shoes | Bag | Blazer

The ribbed high neck tank top, layered necklaces, classic white blazer and platform ankle-wrap sandals make this a modern and totally current look. 

A white button down tucked in with pleated linen khaki shorts

Tuck your button down into your shorts and roll up your shirt sleeves and you have a tailored yet casual, classy tone-on-tone look.

A white button down tucked in with pleated linen khaki shorts

Shorts | Shirt | Shoes | Bag

Raffia slides with a metal buckle are perfect here. With a raffia clutch to match. 

A sweater vest with pleated khaki shorts

This tone-on-tone look is one you’ll see a lot for summer. Just because it’s light on color doesn’t make it less impactful. It’s fresh and breezy. I’m playing up the oversized nature of this sweater by letting it hang straight down. The platform sandals are essential for making this look come together. 

A sweater vest with pleated khaki shorts

Shorts | Shoes | Bag

A black double-breasted blazer with pleated khaki shorts

I’m wearing this double-breasted blazer over a white t-shirt and with those platform sandals again. This look needs the black bag to ground the black blazer and make the look intentional. 

A black double-breasted blazer with pleated khaki shorts

Shorts | Shirt | Shoes | Bag | Blazer

A white button down untucked with pleated khaki shorts

This was a total experiment with embracing the oversized nature of this shirt. The brown sandals and belt bag are key here for making the look pop.

A white button down untucked with pleated khaki shorts

Shorts | Shirt | Bag

The belt bag is essential. It provides the illusion of waist definition, as does rolling up the sleeves, which draws your eye to the waistline. 

Let’s call this look country club safari. 

A striped button down with pleated khaki shorts

A striped button down is perfect with linen khaki shorts for a tailored and preppy look. Once again, these brown accessories make this look come alive. 

A striped button down with pleated khaki shorts

Shorts | Shirt | Bag

A white ribbed tank top and pleated linen shorts

A fitted top that’s tucked in shows off your waistline. This halter tank top also shows off your shoulders.

A white ribbed tank top and pleated linen shorts

Shorts | Shirt | Shoes

An olive green top with pleated khaki shorts

Olive green is perfect with khaki shorts. These platform ankle-wrap sandals make a modern statement with more traditional shorts and a top. They give the look a bit of an edge and make it pop. 

An olive green top with pleated khaki shorts

Shorts | Shirt | Shoes | Bag

Try different combinations and see what you like. Have fun with it!

Infographic shorts summer outfits

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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