How To Wear Cargo Pants And Look Stylish: A Man’s Guide

Learning how to wear cargo pants stylishly isn’t as hard as you might think.

Sure, get it wrong and you could end up looking like a reject from the G.I Joe fan club. However, with the right styling tricks up your sleeve, you can look pretty awesome in a pair of classic American cargo pants.

In today’s article, I’m breaking out my top tips on how to wear cargo pants and look great doing it. So whether you’re looking for a new style to try or just need some inspiration, you’ll discover:

1. A Brief History Of Cargo Pants
2. How Should Cargo Pants Fit?
3. What Can You Wear With Cargo Pants?
4. What NOT To Wear With Cargo Pants
5. How To Accessorize When Wearing Cargo Pants
6. Cargo Pants Outfit Ideas

#1 A Brief History Of Cargo Pants

Cargo pants were first popularized in the military during WW2, when British soldiers came to realize their potential as versatile and convenient battle-wear. Unlike previous military uniforms worn in WW1 and the 1800s, cargo pants were far more convenient and far less ‘tailored’ than the classic uniforms of years gone by.

It wasn’t long until the US military also picked up on this style of uniform and started to produce them en masse for their own soldiers during the Second World War. This is where the really interesting history of cargo pants begins.

France was allied with the US during WW2. As such, we sent across batches of our homemade Cargo pants to the French so that they too could benefit from the tactical convenience of pocketed cargo pants.

However, when France fell to German occupation in 1940, guess who stole those pants to give to their own military units. You guessed it – the Nazis.

Nazi soldiers on board U-boats would wear cargo pants for the same reason as the Brits, Yanks, and French – comfort and convenience on the battlefield. However, when we gave them over to the French, never did we think that the Nazis would get hold of them and start wearing them while sinking our battleships in the middle of the Atlantic!

Since their introduction in the military, cargo pants have become staple style items for men and women across the globe. In the last 50 years, they’ve been worn on the runway, at anti-war protests, and for comfort around the home. In fact, in 2020, they saw a huge increase in popularity when a slimmer-cut version was released to the public.

And they never went away. The slim cargo had its run, then the pendulum swung hard the other direction — wide, low-slung, parachute-style cargos took over streetwear, and the cargo pocket started turning up on everything from nylon trousers to tailored wool. So if you’re wondering whether cargo pants are still in style, the answer is yes. The shape is what changed, and the pair sitting in the back of your closet since 2008 is not the pair you want now. If you want to see where cargos sit next to chinos, five-pockets, and the rest, I laid it all out in my guide to the 15 types of pants every man needs.

#2 How Should Cargo Pants Fit?

Here’s the part most guys skip. The pocket gets all the attention, but it’s the fit through the waist, the seat, and the hem that decides whether you read as relaxed or just sloppy. Those aren’t the same thing, and the gap between them is narrower than you’d think — I broke that down in my guide to wearing the relaxed fit trend without looking sloppy.

Four things to check in the mirror before you buy:

• The waist stays put without a fight. Cargo pants carry their weight low on the leg, so a loose waistband slides all day. If you’re hitching them up every ten steps, drop a size and wear a belt because you want the belt, not because you need it.
• You can pinch about an inch at the thigh. No pinch and they’re painted on, which makes the cargo pocket gap open every time you take a step. Two fistfuls of fabric and the leg collapses into a puddle. One inch is the target.
• The hem stops at the top of your shoe. One break, no more. Cargo fabric is heavy and it stacks fast, and stacked fabric sitting above a bulky pocket makes your legs look shorter than they are. If the pair runs long, a tailor fixes it in a day — worth knowing what alterations should actually cost you.
• The pocket sits on the SIDE of the thigh, not the front. Front-facing pockets add width in the one place you don’t want it. The pocket should land around mid-thigh, roughly where your fingertips fall when your arms hang straight down.

And here’s the rule guys break constantly: the pockets are for shape, not storage. Load one up with keys, a wallet, and a phone and it bulges out sideways, adds three inches to your thigh, and slaps against your leg with every step. Put your stuff in the front pockets or a bag and let the cargo pockets lie flat. On a modern pair they’re a design detail, not a rucksack.

Cut matters just as much as fit, and there are four you’ll actually run into on the rack. Each one sets a different level of formality and asks for different shoes, so pick the one that matches how you plan to wear them.

Buying your first pair? Get the classic straight or the slim taper, in olive, stone, or black. Those two work with the most shoes and the widest range of tops, and neither one dates quickly. The wide-leg and parachute cuts are pulling all the attention right now and they can look sharp — but they need the rest of the outfit to hold up its end, and they’re tough to wear under 5’9″. More on that in my breakdown of whether wide leg pants are still stylish for men.

#3 What Can You Wear With Cargo Pants?

Cargos are the perfect pants for guys who want to be comfortable but remain stylish and well dressed. But how do you wear them without looking like you’re headed out for a day of manual labor?

It’s simple – pair them with the right tops and shoes to make sure you’re rocking them with style.

Remember, cargo pants are not formal in style. In fact, most designs aren’t even suitable for smart-casual environments! For the most part, you should only wear cargo pants when formality isn’t an issue and the name of the game is casual and comfortable.

When wearing cargo pants, pair them with:

• Henley shirts – these are great for a casual look. They sit above the formality of a t-shirt without being too over the top.
• Polo shirts – a step up from a t-shirt and Henley, polos are still very casual but can be dressed up with the right accessories. When wearing them with cargo pants, keep your polo shirt untucked and opt for a fit that matches that of your cargo pants.
• Casual button-down shirts – these can add a touch of formality to your look without making it seem like you’re trying too hard. Opt for earth tones like beige and brown to provide a military-style colorway for your outfit.
• T-shirts – t-shirts are always going to be a great option when it comes to cargo pants. They’re comfortable, they come in a million different designs, and you can dress them up or down very easily. Just make sure your t-shirt fits well and isn’t too baggy.
• Hoodies – perfect for lazy days when you don’t want to think too much about your outfit. Just throw on a gray hoodie with a pair of baggy cargo pants and enjoy the comfort of ultra-casual clothing.

When it comes to footwear, you’ve got a lot of options. Cargo pants work with most styles, except the most formal of shoes. Try wearing your pair with:

• White sneakers – these are always going to be a great option. They’re comfortable and they go with pretty much everything.
• Boat shoes – these have a casual yet stylish look that’s perfect for cargo pants. Just make sure your boat shoes are clean and in good condition before you leave the house!
• Desert boots – another great choice for those who want a stylish but casual look. Again, just make sure your desert boots are clean and in good condition before you leave the house!
• Military boots – if you want to rock a more military-inspired look, then opt for a pair of black or green military boots. Dr Marten boots are a classic style that would work well here.
• Sandals – yes, even sandals can work with cargo pants! Just make sure they’re of a simple design and that your feet are well-groomed and clean.
• No shoes – if you’re just lounging around the house or taking the dog for a walk, then feel free to leave your shoes at home. Just make sure you’re not going to be doing any strenuous activity that might damage your feet!

#4 What NOT To Wear With Cargo Pants

Sure, cargo pants are really versatile. But when it comes to formal wear, things can get a bit more restricted.

To cut to the chase, here are a few things you should avoid wearing with cargo pants:

• Formal shoes – this includes dress shoes, Oxfords, loafers, and any other kind of shoe that wouldn’t normally be considered casual.
• Tuxedos – it should go without saying, but a tux isn’t going to work with cargo pants. They sit on the complete opposite ends of the formality spectrum.
• Suit jackets – again, this should be obvious. If you’re going to wear a jacket with your cargo pants, make sure it’s of the casual variety. If your cargo pants are slim-fit you might be able to pull off a blazer in the right situation, but personally I’d avoid all kinds of tailoring to be on the safe side.
• Dress shirts – a dress shirt is too formal to be worn with cargo pants. If you want to wear a collared shirt, opt for a polo or casual button-down instead.

#5 How To Accessorize When Wearing Cargo Pants

Accessories like belts, watches, and sunglasses are perfect additions to a cargo pants outfit – they’ll help to define your style and take your look to the next level.

Belts can actually help to make you look thinner. When wearing baggier cargo pants, using a belt to tuck your waist in can help to give you a slimmer appearance. If your cargo pants are already pretty slim-fit, then a belt isn’t really necessary (unless you need one to help keep your pants up!).

A watch is always a great accessory for men. It’s practical, it looks stylish, and it can help to make you look more put-together. If you don’t normally wear a watch, then now is the time to start. A military or field watch can be a great way to present a classic army aesthetic and stay true to the classic use of cargo pants in times of war.

Sunglasses are perfect for those sunny days when you’re wearing cargo pants (or shorts!) to the park with your kids. Obviously, they’ll help to keep the sun out of your eyes. However, they can also make you boost that military aesthetic, especially when wearing aviators! Just make sure you choose a style that goes well with your face shape.

#6 Cargo Pants Outfit Ideas

There are hundreds of different styles you can achieve with cargo pants. However, for me, there are a few that stand out as iconic examples of great men’s style.

If you’re looking to really show off your style and set yourself apart from the millions of cargo-wearing guys out there, try putting together outfits inspired by these lookbook ideas.

The Military Man

At the end of the day, cargo pants are military through and through. So why not embrace this and wear an outfit that suits the style of the US military?

To achieve an accurate military aesthetic, pair your cargo pants with a simple white tee or a camo print shirt. For your outerwear, go for a bomber jacket or an army green parka. And don’t forget to accessorize with aviator sunglasses, a watch, and a green canvas belt.

Finish it with sturdy combat boots and tuck the shirt in. A tucked hem shows the waistband and keeps the eye on the pockets instead of a pile of loose fabric at your hips. A structured ball cap works here too.

The mistake here is stacking every military cue at once. Camo shirt, field jacket, dog tags, combat boots, and cargo pants together stops being an outfit and starts being a costume. Pick two cues, keep the rest plain, and you land on well dressed instead of reenactor. One more detail nobody mentions: keep the hardware matte. Shiny buckles and polished brass look like a rental. Flat black, olive drab, and brushed metal look like the real thing.

The Athlete

Cargo pants are often associated with being comfortable and relaxed. So why not put together an outfit that’s perfect for a day spent doing some light exercise?

Start with a pair of loose-fit cargo pants in a dark color like black, navy, or grey. Then add a moisture-wicking t-shirt in a bright color. For your shoes, go for a pair of running shoes or trainers.

Add a lightweight zip-up hoodie when it turns cool. And pick a nylon or poly-blend cargo over heavy cotton twill for this one. Cotton soaks up sweat and gets heavy, and a heavy cargo pocket flaps around every time you move.

A cap and a pair of sunglasses finish it off. Then empty the pockets before you head out. Nothing wrecks this look faster than a phone slapping your thigh with every stride, and loading a cargo pocket up is the quickest way to stretch it permanently out of shape.

The Cali-Cargo

California is known for its surf. Even if you’re not from the golden coast, you can still channel that surfer vibe by wearing a loose-fitting vest-top, loose cargo pants, and sandals. After all, it is California we’re talking about – the land of eternal summer!

To get that Cali-cargo look, start with a pair of beige or white cargo pants. Then add a black or white vest-top. And finally, slip into a pair of easy-to-wear sandals like Birkenstocks. Accessorize with a beaded bracelet and sunglasses to finish off the look.

A lightweight denim jacket over the shoulders handles the temperature drop once the sun goes down, and a wide-brim straw hat beats a ball cap in this outfit every time.

One warning on the pale colors: beige and white show every mark, and sand, sunscreen, and salt water are brutal on them. Buy a pair you are willing to wash often, and skip white altogether if you have kids in tow. Stone and sand-colored cargos give you the same easy summer look and hide a lot more.

The 90s Cargo

Cargos were pretty big during the 90s. There’s no shame in bringing that look back and pairing your cargo pants with some classic 90s staples.

Start with a pair of light cargo pants. Then add a black or white t-shirt, and slip into a pair of chunky black sneakers. For your outerwear, go for a denim jacket or hoodie.

Will this style work in warmer climates? Probably not – but it’s perfect for those cold winters where layers are key.

Tie a plaid flannel around your waist if you want the full grunge treatment, and a beanie or bucket hat earns its place once it gets cold.

Two things to watch. First, the 90s cut was baggy everywhere, and head-to-toe baggy on a modern frame just reads shapeless. Keep the top fitted and let the pants carry all the volume. Second, skip the choker. Some of the 90s should stay in the 90s.

Looking for military inspiration in your wardrobe? Check out my guide to 11 styles items with a military heritage.

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