Ask Esquire: What Are The Rules Of Wearing Cargo Shorts

Poor Leonardo DiCaprio! He's having a tough week.

First, the new book Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World detailed how he was bamboozled by a grifter, who showered him with expensive gifts, which he then turned over to the government after learning of the fraud.

Also, Chris Martin, conscious uncoupler and singer of maudlin tunes, performed a new song about Leo's love for cargo shorts, effectively calling him out as a dude-bro-nerd.

How dare this Martin, who is not even the superior Martin (that would be Ricky or Donna), make fun of the forever bachelor, innovator of how to carry things, and Academy Award-winning actor, who played Arnie Grape in What's Eating Gilbert Grape and that guy who can't hold onto a piece of floating wood to save his life!

But let's listen to a snippet of the song: 

The little ditty, which Martin performed at the 20th anniversary gala of the Leonardo DiCaprio Foundation, has also put the spotlight on the pimple of men's fashion, the cargo shorts. The controversial piece of clothing is regarded as never a good look, but it continues to thrive on the legs of men, popping up (like a pimple!) again and again, over and over, forever amen.


Men who wear cargo shorts ask: What are the rules for wearing cargo shorts? Should we even dare?

It would be easy to say, “Do not fudgin' wear fudgin' cargo shorts, goddammit!” but we've been open-minded of late, what with the return of pleats, the revival of khakis, and the rise of baggy trousers. Like DiCaprio, the much maligned shorts can also be a winner. You just have to choose the right one. 

The fit is trim

We're going to make it easy for you and put forth the same rules of the vanilla version: Keep it slim. The main gripe about cargo shorts is that they look like you've strapped on parachutes around your legs. The solution is choosing a pair that is more tailored (but not tight), something that will not make you look like you're waddling through an invisible marsh.   

The length is short

As in, this thing should end above the knee. We refer you to this fantastic visual guide on inseams (or shorts length) by Esquire US. A five-inch inseam, which floats around mid-thigh, is the shortest you can go without offending (or exciting) other people. A nine-inch inseam terminates just above your leg knobs, but if this longer pair breaches your caps (or if you are not tall), go higher.  

The pockets are thin

Cargo shorts are a spin-off of cargo pants, which, as part of military dress, feature large, expandable patch pockets that provide storage for gear. In this context, the size is understandable (you'd want your map and compass handy when you're in battle, right?), but for civilian life, those pockets should be adapted. Something thinner and smaller is better.  

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The pockets are light

It would be very tempting to shove your entire life down the abyss of extra pockets, but don't. Their very existence and also their placement on the bottom half and by the side of cargo shorts already add heft. And if you stuff, say, a baby's dirty diaper down there, you're just packing on more lumps and bumps to your already irregularly shaped body. So what can you deposit in your cargo shorts pockets? A piece of paper, three coins, air.   

The thing is clean

Because they're comfortable, they tend to become your favorite pair. Over time—and without washing—the color turns into gray gloop, holes appear, stains assert themselves. A piece of garment in this state does not belong on your body.

The style is appropriate 

As a creature borne of crawl-in-the-mud utility, these don't belong in the office or a fine dining restaurant—unless your place of work is a hardware-slash-burger joint. The cargo shorts, like other shorts, are best for the easiness of weekends or any period of time when you don't see your boss. You can wear it with a T-shirt, but we find that  something with a collar like a short-sleeved shirt or an 85-year-old polo shirt looks smarter. To take them further into preppy zone, pair with loafers.   

One more thing

Now, finding a pair of cargo shorts that fulfills all of the above is like looking for a kind soul at a fashion party. It's not easy. We'd go with retailers that don't trade in adventure or sports for trim-and-slim cargo shorts. A quick search online yields a last-season pair from Spanish high street label Mango. It's on the longer side, but it's on final sale. Grab it while you can.

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Clifford Olanday
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