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How To Wear Cargos Without Looking Like You're Going Through A Midlife Crisis

Sure, cargo pants are practical and comfortable, but when styled inappropriately, they can make you look like a sad tito
by Dyan Sheryl Carolino | Feb 22, 2017
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Ahh, cargo. These boxy pants based on British military trousers of the ‘30s was brought to our country by Old Navy, in their quest to make us all look like blobs.

This piece of clothing is particularly popular with men, as they tend to place a more utilitarian focus on your fashion selections. Cargo pants are also “the great equalizer”—they fit (not!) all shapes and sizes, and they appeal to men’s overriding personality traits and priorities: practicality and carelessness.

The problem with cargo styles is that if left unchecked, they can rob you of your youth and morph you into a certified tito. No, not the brother of your father or mother, or the husband of your aunt. This tito:

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Fortunately, you can still wear this versatile and comfortable piece of clothing without looking old-fashioned. For a complete guide on how to wear cargo pants, including outfit ideas and some common styling mistakes, check out the suggestions below.

Timing is everything

As with any other piece in your wardrobe, the key to looking good and polished when it comes to cargos is timing. Obviously, if you’re walking your dog around the village or drinking at home with friends, cargo pants or even cargo shorts is okay. But if you’re heading down to the club or going to the office on a casual Friday, swap them for the more proper jeans or chinos.

Make sure you have the proper hemline

Originally, cargo pants had drawstrings at the bottom, which could be drawn tight to keep the hem secure at the top of your shoes. This was important in the military, as it helps soldiers prevent dirt from getting up inside their pants or into their boot.

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The cargos we see now don’t have this feature. So, make sure to wear one that’s not too high or too low, and make sure it won’t get caught under your shoe or will drag on the ground. Not to mention, hems that are too low will prematurely wear out and create a ragged appearance, making you look like a total tito.

A slim fit is the best fit

Loose cargo pants are so ‘90s, and definitely won’t do you any favors. Go for slimmer leg lines and fewer pockets, which will give you a trim sillhouette.

To style slim-fit cargo pants, treat them like cotton chinos. Pair them with T-shirts, casual blazers, and v-necks, or put on a sport coat. Don’t use those pockets, too. Ironic, but you need to keep the cleanliness and sleek lines of the pants to make it work.

If you're still looking for places to keep your good morning towel or your bulky, brown leather wallet, just carry a bag like everyone else.

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V-Necks, Casual Jackets, and Converse

Finding the right piece to wear with cargos can be difficult. Here’s the rule of thumb: don’t use pieces that are formal and business-like, such as smart shirts, blazers, and dress shoes. Just choose really simple pieces. Stay away from busy patterns and colors. Opting for plain and simple shirts is your safest bet.

Throw on a casual jacket if you wish. Leather jackets can especially add a touch of sophistication and can easily turn your daytime attire into evening wear. If you’re wearing more neutral-toned cargo pants, a khaki colored bomber jacket would be a real nod to the military style while keeping the look fresh and modern.

As for the shoes, go for trainers, Vans, or a pair of low-cut Converse. These will keep the look edgy and modern yet simple, while allowing you to enjoy comfort.

Camouflage Prints

Nothing screams tito like the khaki and dark green shades of camouflage prints. But camo cargos are making a revival, no one knows why, as designer and high-street retailers are releasing designs in this pattern. So, make sure you don’t miss out.

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Avoid styles with longer lengths, however. The last thing you want to do is look like a child pretending to be Action Man. Go for shorter and more neutral colors, too—very pale beiges, light browns, and greens—to avoid clashing.

Pocket Sizes

Despite what you may have heard, size does matter—when it comes to cargo pockets, that is.

Pockets that are too big will make the pair of pants or shorts look way too juvenile or sporty. Pockets that are too small, on the other hand, can make it overly dressy. Remember that cargos are for casual and laid-back outfits, not sporty or sophisticated, so go for modestly sized pockets.

Avoid those that have an expansion fold on the bottom edge, and make sure these pockets lie closer to your thigh and look subtle.

No doubt, cargo pants and shorts are extremely difficult to pull off. To many, they're '90s rejects and worn by men who have landed themselves in an imaginary midlife crisis.

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But times are definitely changing. With proper styling, even the most sratorially clueless tito can get away with.

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