JEAN QUEEN The writer, who has been compared dauntingly to both Susan Sontag and Joan Didion, wearing her beloved shorts in her Brooklyn neighborhood. Photo: Leeta Harding for The Wall Street Journal

GROWING UP IN Texas, I attended an evangelical private school whose thorough strictness was expressed most clearly in the dress code. Boys wore slacks; girls wore pleated skirts in khaki and slate gabardine; for weekly chapel, everyone wore white oxford shirts and loafers. Summers, after so much starchy biblical confinement, came as an all-consuming release. This was Houston, and so it was mostly humid and hot to the point of unearthliness—three-digit temperatures were normal for months. But I loved the heat, the burning dazzle during the daytime, the way the grass stayed warm long into the night. On my suburban cul-de-sac, with its tiny pirate-ship playground and built-in gang of like-minded neighbors, you could play outside every minute you weren’t sleeping. And so, on the first day of summer, I’d ceremonially put on a pair of cutoff jean shorts and a T-shirt—what deep spiritual freedom!—and for months I’d hardly take this other, far more satisfying uniform off.

Today, I live in Brooklyn, N.Y., not Houston. But to the chagrin of many of my loved ones, I still wear jean shorts as often as I can. I don’t look good in them, really, not like (for example) Jodie Comer as Villanelle in “Killing Eve,” pulling up to a Tuscan villa on a motorcycle in a sheer blouse and flawlessly hip-hugging cutoffs, then making herself a snack to cap off the pleasure of the journey and glowing with the irrepressible sensual energy of someone who knows how to do everything right. (Daisy Duke, played by Catherine Bach on “The Dukes of Hazzard,” of course set the standard for looking terrific in now-eponymous tiny jean shorts, but I don’t think about her much—I grew up amid enough ambient fondness for the Confederacy that I now prefer to leave anything related behind.) I’ve actually been trying to find a pair of shorts like the ones Villanelle wears in that “Killing Eve” scene—they’re from Paige Denim, or so says the internet. I ordered a couple of pairs, but then I returned them. They were too nice for me; they made me feel like I was trying to look good, which is the opposite of what jean shorts are supposed to do.

‘They made me feel I was trying to look good, the opposite of what jeans shorts should do.’

My preferred pair of jean shorts is so beat-up—so frankly disgusting—that there is no way that anyone could mistake me for a person making an effort, not even of the good, socially requisite, bare-minimum sort. They’re from OneTeaspoon, a brand that specializes in ostentatiously distressed and slouchy denim, which was founded in the Y2K era by a then-21-year-old Australian woman named Jamie Blakey. (“Just get some scissors and sand paper and rip in,” Ms. Blakey told retailer Urban Outfitters when prompted to give denim-customization tips. “The blunter the scissors the better. A big bottle of cheap bleach is always good to have on hand, too.”) OneTeaspoon’s jean shorts make the wearer look like a former Disney starlet having a breakdown in front of the Los Angeles department store Fred Segal, or a 22-year-old throwing away drugs at the airport on her way back home from a music festival. Roughly speaking, this is not an aesthetic that an adult woman should either replicate or aspire to. And yet, when I think about my jean shorts, all other clothing starts to feel like gabardine and chapel—like something you submit to, often because a code requires it, and that you run from as soon as summer sets you free.

I hope, one day, to be able to measure my life out in jean shorts. My elementary-school pair was black, mid-thigh, frayed at the edges. When I was a teenager, my jean shorts were medium-blue, whiskered, and low-rise in that terrifying early-aughts way. Now my most dearly beloved pair is a pale, bleached-out color, and so short that the pockets hang down below the rolled-up hems (I told you they were disgusting!). They’re loose, with a waistband that rides on the middle of my waist as easily and comfortably as you’d drape an arm over a friend’s shoulder. The odd fit—the disturbing combination of tiny and baggy—has prompted multiple friends to call these shorts my “jean diaper.” Last year, my boyfriend started calling them my “diapies,” in an attempt to shame me out of wearing them in public. As he might have predicted, this tactic backfired, and made me want to wear the shorts more. In my attitude toward my jean shorts, I now resemble Tobias Fünke, David Cross’s therapist character on the TV comedy “Arrested Development”—a self-professed “never-nude” who took showers with his booty swathed in cutoff denim. I feel more purely myself in my jean shorts than I could in any other attire (or lack thereof).

I have resigned myself to the fact that, even with my general disregard for sartorial propriety, I won’t be able to wear my current pair of jean shorts forever. But I’ll just get a new pair. And listen, maybe they’ll be even worse.

JORTS FOR THE APOCALYPSE / Barely Anyone is Immune to the Charms of Extreme Casualness if You Stoop to the Jean Short, Try These Decent Options
Clockwise from top left: For a pleasingly slouchy fit Shorts, $225, moussy-global.com; For an almost-elegant, dark, cuffed look Raey Shorts, $103, matchesfashion.com; For a convincingly whiskered wash Shorts, $69.50, levi.com; For a neat oyster shade Citizens of Humanity Shorts, $178, freepeople.com Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Anne Cardenas

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