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What Style of Shoes Go with Cargo Shorts?

Black and white studio image of person in cargo shorts

Cargo shorts are one of the easiest clothing items to wear and yet, they’re one of the hardest to style. They are so comfortable and they can go anywhere but it’s always so difficult to know what to wear with cargo shorts. What style of shoes go with cargo shorts, anyway? Learn how to style cargo shorts so that you always look effortlessly fashionable and ready for any situation that might arise. Because no matter what happens, it definitely helps if you look great while it’s happening.

Who Wears Cargo Shorts?

As soon as you see cargo shorts, you know it. They’re easy to immediately identify and if you’re like most people, you’ve worn a pair of cargo shorts at least once. These shorts were the “it” look of the 1990s and then became a matter of worldwide style discussion in recent years. Who wears cargo shorts? At some point, everyone. But cargo shorts are still widely associated with skateboard culture, construction workers, anyone who is doing tough work and people who are enjoying outdoor activities. Cargo shorts are a perfect match for hiking, for example. They’re great as workwear, casual wear, outdoor wear. They may be the perfect summer shorts…depending on who you ask.

Outside on the beach in cargo shorts

Anyone can wear cargo shorts and everyone has. Men, women, children, people who are stylish and people who aren’t so stylish. Once, cargo shorts were even high fashion, with several well-known designers creating their own high-end styles meant to impress the fashion world. In recent years, cargo shorts have become much less trendy and some say that in modern fashion, cargo shorts are simply the worst. But many people say that cargo shorts are perfect because they’re functional and comfortable. In fact, that’s why cargo shorts were made in the first place. Where do you stand on cargo shorts? Get to know more about the history of cargo shorts and see how this style has evolved over the years before you make your final decision.

A Quick History of Cargo Shorts

Cargo shorts just feel like they’ve always been around. You almost expect someone to show up wearing cargo shorts in a movie about people in the 1700s. That’s how common it is to see cargo shorts. But actually, they’re pretty new on the fashion scene, especially when compared to other types of shorts. While it seems like their history must go back pretty far, they’re actually very, very modern. Even their earliest origins don’t go all that far back in time.

Short pants, or shorts, were widely worn in the 1800s, but not by grown men or women. They were worn only by young boys, in fact. In Europe, it was customary for young boys to wear short pants even in the winter. That’s because a boy did not put on long pants until he was old enough to be considered a man, or at least a young man. It wasn’t until late in the 1800s that it became acceptable for grown men to wear short pants, which first debuted on the golf course and in other athletics of the day. After athletes made shorts acceptable, they started to appear everywhere and they truly caught on in the fashion world.

Cargo pants, which were pants featuring at least one large patch pocket that could be used for storage, were created in the 1930s by the British military. The pants were somewhat baggy and had a large pocket right on the thigh, on the top of the leg. This pocket was extremely handy for storing extra ammunition, rations and other necessary items. These were the first cargo pants known to have ever been widely produced and worn. They were so successful, the British military continued using this exact design for their soldiers for another 25 years.

Wearing cargo shorts by the water

The U.S. military noticed the innovative pants design and immediately copied it. They also added to it. American paratroopers first wore military-issue cargo pants that had dual pockets, one large pocket on each leg, which doubled the storage space of the British design. Soon, all U.S. armed forces were wearing standard-issue cargo pants.

But when did the long cargo pants that were so popular with the military turn into shorts? That actually wouldn’t happen for several decades. Cargo pants, worn so much by soldiers, started to catch on with the public in the 1960s. Soldiers returning from Vietnam helped make cargo pants popular as everyday wear. Soon, people started wearing them for work and for regular daily looks. But as popular as cargo pants were back then, they still didn’t turn into shorts.

Cargo shorts didn’t appear on the fashion scene until the late 1980s. Made in khaki with the distinct patch pockets, cargo shorts joined the strange fashion of that decade and were ready to make their mark. It was in the 1990s that cargo shorts really found their style…and everyone put them on to show off their swagger.

Being Trendy

In the 1990s, pretty much everyone wore cargo shorts. Baggy and somewhat bulky, loose and comfy, cargo shorts were the style choice for skateboards, cool young people, hot and trendy stars, recording artists and pretty much everyone who wanted to look fashionable. Once cargo shorts appeared on the style scene, that was it. This fashion item became a star of style trends and now, everyone recognizes cargo shorts. But if you’re going to wear them, it helps if you do it well. What style of shoes go with cargo shorts? You actually have a lot of options for styling your shorts well.

Which Shoes Should You Wear With Cargo Shorts?

So what should you be wearing with your cargo shorts to style great-looking outfits? Shoes make or break any outfit. You want to pick the right shoes to finish off your cargo shorts because wearing the wrong shoes will ruin your entire look. No matter how carefully you choose the clothes, be even more careful when it comes to the shoes. Get the right shoes and you will have the right look.

Basketball Shoes

Nike Air Jordan Access Mens Basketball Trainers AR3762 Sneakers Shoes (UK 7.5 US 8.5 EU 42, Black Gym red White 001)

Basketball shoes and cargo shorts are truly a perfect match. Cargo shorts are the end-all, be-all of casual style and so are basketball shoes. These two were just meant to be together. Khaki cargo shorts pair perfectly with literally any basketball shoes in any color or design. You can also play around with mixing and matching colors in your shorts to colors in your shoes. Just remember that one color in each item should match. If there’s a little bit of red in your shorts to match with the red in your shoes, that’s style.

You can wear basketball shoes and cargo shorts with any type of socks in any length, from no-show to crew length to long tube socks. It’s a great combination that’s versatile and works well as a casual look for any daytime or evening summer gathering.

Boat Shoes

Sperry Men's A/O 2-Eye Boat Shoe, Sahara, 10 M US

With a pair of no-show socks, boat shoes are an absolutely perfect choice for your cargo shorts style. Boat shoes are low-cut shoes with rubber shoes that have a very distinct style. Often, they are made with laces that go around the sides, peeking out at intervals along the design of the shoe. The look is casual but it has a lot of flair and it puts any cargo shorts outfit right over the top, syle-wise.

This is a great look for boating and being out on the lake, obviously. It works for fishing and any water-related activity, even if you’re hanging out poolside. In other words, it’s a perfect look for all sorts of summer fun and pretty much any water-related activity of any type.

High Heels

The Drop Women's Avery Square Toe Two Strap High Heeled Sandal, Natural, 8

Cargo shorts are associated with casual style, working style, rugged style. But you can successfully pair this casual fashion item with high heels. Actually, this creates lovely contrast. The glamorous style of heels, whether they’re closed-toe or strappy, can look great against the more casual look of cargo shorts. Try pairing neutral cargo shorts in olive green or khaki with brightly-colored heels to create a fun summertime look. Heels are a perfect way to add a bright pop of color to any look.

Match this with a sleeveless blouse and a pair of sunglasses and you will have a casual but highly stylish summertime look that’s great for a casual evening out with friends. You can wear this look anywhere that you want to be a little bit glamorous but still show off a fun, casual style.


Sperry Men's Gold Cambridge Penny Penny Loafer, Amaretto, 7

Is there anything that can’t be worn with loafers? Considered by many to be the perfect casual shoe, loafers come in styles that are made for both men and women. Wear them with no-show socks and your cargo shorts to capture a look that’s casual but also classic. You’re showing that you definitely have a great sense of style but you know how to relax and enjoy your fashion.

Loafers are easy to wear and they do go perfectly with everything, so always keep a pair in your closet. Any time you need a good cargo shorts look, slip into your shorts and your loafer and a polo shirt. You will look fashionable and classic and elegant all at once.


CUSHIONAIRE Women's Mandy Cork Espadrille Wedge Sandal,White,9

When it comes to summer fashion, there’s really just one word to remember: sandals. Of course, they’re a perfect match for cargo shorts! They’re casual, they look great for summer days or nights and you probably already have more than one pair in your closet. Whether you like flip flops or gladiator sandals, put them on, wear them with cargo shorts and you will be ready for all sorts of summertime events. This will look great with a T-shirt, a tank top, a button-down blouse or anything else you want to wear with your cargo shorts.


adidas Men's Adilette Shower Slides Black/White/White 13

The whole point of cargo shorts is about capturing a look that appears to be effortless but that is also, of course, quite stylish. Nothing says stylish and effortless like slides. You just slip your feet into them and go. And while conventional fashion wisdom says that you can never wear socks with sandals, this rule doesn’t apply to slides. Go ahead and put on your crew socks and then slide your feet into those slides. Wear them with cargo shorts and you will look very effortless and casually stylish.

This look is perfect for hanging out with friends but not for doing much else, since those shoes definitely can’t take on a lot of walking or sudden movements. But if you’re looking for a good lounging style, this is it.

White Tennis Shoes

adidas Women's Advantage Tennis Shoe, White/White/Copper Metallic, 8.5

Create a look that’s just classic and simple with a pair of plain white tennis shoes. Paired with khaki cargo shorts and a white T-shirt, this outfit absolutely cannot go wrong. The shoes will work with socks in any length and they will look great in any style, from minimalist canvas designs to bulky basketball shoe styles. Just look for something all-white to create that bright, dazzling look that others will notice. This is a look that’s meant to pop and et still be understated at the same time. They say that simple elegance is a style that’s hard to capture. Well, this look will do it with ease.


Are you surprised by all the stuff you didn’t know about cargo shorts? What about all the stuff you still don’t know? Get the answers to the most-asked questions about cargo shorts and get to know all the things you should know about this famous piece of fashion. Soon, you will be an expert on creating cargo shorts style.

YAXHWIV Mens Tactical Shorts 11" Waterproof Hiking Fishing Breathable Quick Dry Cargo Short Shorts Regular(NO Belt) Khaki

Can cargo shorts be formal wear?

Cargo shorts are accepted as casual wear anywhere you want to go. But when it comes to styling cargo shorts as semi-formal or formal wear, even wearing them to a job interview, don’t. Cargo shorts are meant for casual wear only. They don’t even qualify as business casual because they’re just too casual for that. No, you cannot wear cargo shorts as formal wear. Not unless you want to make a bad impression on others, anyway.

That said, younger stars have attempted to pull this look off on the red carpet by pairing cargo shorts with tuxedo jackets and other elements of formal style. Young celebs trying to cultivate a certain look might wear cargo shorts. And even with lots of money and fame, it still looks bad from a style standpoint. Can cargo shorts be formal wear? No. Sometimes, fashion rules can be bent and there are gray areas when it comes to cultivating your own personal style. But in this case, that’s not the case. Cargo shorts just can’t be formal wear. If you wear them to a formal event, you are likely to offend the host of the event. Definitely don’t wear them to a wedding, unless it’s a casual beach wedding where the attire is strictly stated as beach casual.

However, you can wear cargo shorts as casual clothing just as much as you want and anywhere you want with a casual dress code!

What are cargo shorts made of?

Cargo shorts can be made with any material. They’ve even been made out of leather. However, lots of cargo shorts are made with study fabrics like cotton duck, denim and cotton-polyester blends. This material is comfortable but breathable and it can be lightweight but it’s also very wear-resistant. Since cargo shorts were originally designed to be worn as workwear, they are often still made with tough materials so they can serve this purpose.

How should cargo shorts fit?

Cargo shorts by nature are made to be a little bit baggy through the hips and legs. Mostly, you want to make sure cargo shorts fit around the waist. Cargo shorts are designed with different rises, as are pants. Make sure the rise of the pants sits in the right spot on your body. Cargo shorts will either be high rise, sitting a little bit above the belly button or mid-rise, sitting right at or under the belly button or low-rise, sitting a couple to a few inches below the belly button. Make sure the cargo pants fit around the waist with no gapping and no bunching and you know you have a good fit.

The length of the shorts should also be right. Because of the large pockets, most cargo shorts are somewhat longer in the inseam than other shorts styles. They usually fall somewhere from just above to just below the knee. To make sure your shorts fit, sit down and bend down in them. They should still provide you with coverage around the legs and should not be too tight or too loose, no matter how you sit and move around.


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