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How to Wear Shorts That Don’t Look Dorky

Here are the shorts Gen X women love (and don’t love) on their men

Bob Marley, Michael Jordan, Taye Digs, Lemmy Kilmister, Denzel Washington: all wearing shorts
Jean Bernard Sohiez/urbanimage.tv, Andrew D. Bernstein/NBAE via Getty Images, Jason Smith/Everett Collection/Alamy Live News, George Bodnar/IconicPix, Marbella Photo/Shutterstock

In the course of reporting this article (by which I mean polling all my major group texts), I’ve come to realize a couple core truths: First, I’ve learned that I am deeply conservative when it comes to men’s thighs and feet. In my estimation, neither should be exposed except while showering, having sex or being inspected by a medical doctor. And second, there’s just no real consensus on what style of shorts counts as sexy or even “acceptable when worn by men.

Let’s make a few things clear at the top: I’m talking specifically about Gen X dudes. The youth of today, as unfettered by middle-aged spread as they are by notions of gender, may dress as they see fit. But if you’re old enough to have a favorite Breakfast Club character, there are rules. And because nothing in this life is easy, the rules are wildly subjective and can change on a dime.

To wit: My husband, a gentleman of a certain age who works from home, is an Always in Cargoes man. His daily uniform is black cargoes, black T-shirt, and yes, he does run a record label. As a woman who imprinted early on East Coast hardcore dudes, this uniform is agreeable and sexy … to me. (As a side note, do not google “old hardcore dudes.” What comes up is not Ian MacKaye.)

But when polled about the major shorts groups — cargo, Bermuda, cycling, gym — I was shocked to find that most of the women I know were a hard pass on the cargoes. Do you jerks not like pockets? 

Only one other woman shared my affinity for them. (Curiously, she’s also named Emily.) “I’m weird. I like cargo shorts. They make a man seem handy and low-maintenance,” she explained. “They could have anything in their pockets! It’s the Advent calendar of clothing.” But according to my friend Lauren: “There has never been a sexy cargo short. When you’re wearing a cargo short, there is zero attempt at sexiness.”

A few nonnegotiables emerged.

● Pleats: universally despised. 

● Shorts should generally be of a solid color. Don’t go funnying around with stripes or florals. 

● Nobody wants to see a man in bike shorts. 

● The only man allowed to wear short-shorts is Kevin Kline, and then only in the Big Chill

● Classic gym shorts — those baggy little numbers that show a ton of leg — are also out, unless you make a modification: bike shorts under gym shorts. In my opinion, this is doubling down on a bad idea, but to quote yet another Emily: “Cycling under gym shorts is definitely hot: says someone means business and has a jiggly package.” If you’re a man who wishes to convey both seriousness of intent and jiggliness of jiggleables, this is the look for you.

The author, Emily Flake
Generation Sex: Emily Flake answers your burning questions about love, marriage, and midlife sex. Send your queries to aarparrow@aarp.org. / Matt Salacuse
/ Matt Salacuse

If, however, you wish to present as a regular guy and not a sex deli, your choices are few and tightly bound by convention. I recorded several variations of a preference for a “classy Bermuda” — a no-fuss, slim-fitting look with a flat front that hits just above the knee. Because these shorts are so aggressively neutral, they can take on personality flavors as effectively as a poorly wrapped baked good in an underperforming freezer. They lay a base from which your shoes and T-shirt choices can do much of the heavy lifting. 

Normcore stalwarts like J.Crew and L.L.Bean can supply you with well-made, sturdy versions, and you can sub out the boat shoes (yuck) and polos (Ivy League date-rape vibes) they’re usually paired with for, say, a graphic tee and Vans, if you’re trying to hold on to your youth in one hand and your dignity in the other. 

The wild card here is, of course, cutoff jean shorts. As with most things in life, attitude is key. These can skew “sloppy, depressed basement dweller” in inconsiderate hands, but done correctly, they can represent the best of what the dirtbag universe has to offer, which is Lemmy

If you’re one of those ropy fellows who’s only gotten ropier with age, this look is available to you, provided you’re willing to really commit to the facial hair and the well liquor. These are best worn without underwear, and preferably accentuate a package that is not so much jiggly as barely contained. Motorcycle boots and loose morals are mandatory.

These are guidelines, of course; only you know what best suits your frame, your vibe and the preferences of those who have to look at your butt. But if you take anything from this article, please let it be this: No matter what style of shorts you wear, you have to wear real shoes. No sandals, no flip-flops. Call it a tax you pay on your patriarchal privilege, or just call it decency. Free the thigh if you must, but keep those feet under wraps.

Follow Article Topics: Sex-&-Relationships