It’s Time to Face Your Fears and Embrace Jean Shorts

It’s time to talk about something very, very spooky: jorts. Jean shorts, if you’re old-fashioned. A touchy topic, to say the least, and the scariest garment in menswear, in the humble opinion of this very menswear editor, because few things in this world are harder for men to pull off.

Friends—why have we been wearing our jorts in such unappealing ways for so long? Jean shorts get a very bad rap, but it’s because people tend to style them very badly. You don’t need to shy away from the summer staple, though; you just need to figure out how to wear them stylishly! Don’t worry, because I’m here to help you, and I consider myself to be the number-one authority on the topic (mainly because I don’t think anyone is thinking about jorts as much as I am).

Let’s make a vow to wear jorts with intention this summer. There’s a right way to wear ’em, and that’s what we’re going to do from now on. Too many times do I see men walking around in ill-fitting, way-too-long or wayyyy-too-short jorts, and I wonder, Did you look in the mirror before leaving the house this morning? or, more likely, Did you lose a bet that requires you to wear these shorts as a ritual of public humiliation? Here’s my promise to you—if you follow these guidelines for wearing jorts, no one will ever look at you and wonder that again. Let’s get into it.

Images Press//Getty Images

An iconic moment for jorts: Andre Agassi wearing a super-short pair at the the 1988 U.S. Open.

Step One: Length

Arguably the most important aspect of wearing jorts: the length. How long is long enough? How short is too short?

In my books, jorts should typically hit at or above the knee. There is a time and place for a below-knee jort—more on that later—but to be on the safe side, you don’t want to go too long unless you’re channeling the likes of Adam Sandler or Justin Bieber. Plus, at a certain point, too-long jorts kind of just look like cropped jeans instead of shorts, so what’s the point?

You don’t want to go too short either. I usually don’t see this as a real issue, though. Especially with Paul Mescal bringing back the super-tiny inseam, short shorts are arguably more stylish than ever for men, even if they are denim. But mostly, a nice, in-between length will serve you well. Something just above or at the knee is hard to find issue with, even when you’re as picky about jorts as I am.

prada spring/summer 2025 menswear fashion show – arrivals and front row

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Take note of Marc Forne’s jorts at Prada’s Spring 2025 show—a clean, dark wash with a straight leg that grazes his knees.

Step Two: Silhouette

After length, we’ve got to think of the silhouette of your fit, starting with your jorts.

This is where longer jorts are allowed—the only time when it’s acceptable to wear below-the-knee jorts is when the proportions of the rest of your outfit complement it. Super-long jorts and a super-long, baggy shirt? With chunky sneakers? Don’t make me gag.

But! Super-long jorts with a cropped, fitted shirt? Maybe a boot with a slight heel or a slim pair of sneakers to provide some visual contrast? Well, you’re golden, babe. Colman Domingo, pictured below, aces it—loose and baggy on the bottom, tight and fitted on top. It balances out your whole silhouette so you aren’t drowning in your clothes, unidentifiable beneath swaths of jort-y denim.

If you’re going for a shorter pair of jorts, you still have to think about the silhouette. Are your jorts tight and form-fitting (they should not be even remotely close to sticking to your thighs), or are they a little bit more relaxed (the right answer)? Do they have a straight leg, which looks great with most tops, or a wide one, which is better with something more fitted on top? It’s all about finding a balance that creates some visual harmony: not too slim, not too baggy.

louis vuitton: photocall paris fashion week menswear spring/summer 2025

Julien M. Hekimian//Getty Images

Colman Domingo expertly pairs his wide, baggy, long jorts with a heeled boot and fitted top.

Step Three: Styling

Jorts alone don’t make a fit. You’ve gotta level ’em up with something good.

Loyal Esquire readers will know that I am always a proponent of the double-denim look, which, in the year of cowboy-core, is more relevant than other. Grab a denim jacket in a similar wash to your shorts and pair ’em together for a clean, cool, and collected look. Ncuti Gatwa demonstrates below with ease.

If you don’t want to go denim-on-denim, though, fear not. You can still style your jorts in a way that doesn’t scream, “It’s 2009 and I just moved to Williamsburg and discovered what a man bun is!”

In the dog days of summer, staying cool and looking hot are key factors to getting dressed. With your denim shorts, long or super short, consider a bicep-baring tank top or a T-shirt that has a slightly cropped hem. Tie a bandanna around your neck, if you feel like it, or stick to accessorizing with sunglasses and a baseball cap.

You can also get away with a clean white tank top and a crochet or knit polo on top—it’s casual, but it doesn’t look like you didn’t even try. And if you’re reading this, then you did try and will continue to try, lest your jorts get the best of you.