Harrison Ford keeping it casual at the Cannes Film Festival. Donald Glover strolling in downtown Manhattan. Ralph Fiennes emerging from a sandstorm in The English Patient. Paul Newman grabbing a couple beers for the road. Ralph Lauren biking with his son in Montauk. Each one, an example of a style icon wearing shorts, and a living, breathing retort to Fran Lebowitz, who perhaps spoke for many when she said that men wearing shorts is, and I quote, disgusting. None of them, you’ll also note, is particularly close to a body of water, which some propose as a guideline for when a man can wear shorts. Instead, they’re in the desert, out in nature, or even (gasp!) in the city. And none of them is especially young in these photos, either—they’re in the full bloom of early middle age, well-established with careers, families, and, in some cases, a distinguished touch of grey. For them, wearing shorts might be a form of rebellion against the Lebowitzes of the world—but it looks as natural as can be.

Once upon a time, though, I was more of like mind with Ms. Lebowitz—for years, my bare knees were rarely exposed to the sun, aside from a rare trip to the beach or a pool. I didn’t even own shorts for a spell. And yet, as I’ve aged—and as the planet has warmed, and as dress codes have become less formal—not only do I now possess shorts, I have a full rotation of them, ready to wear the moment the forecast calls for a high above 70. Somewhat like Mr. Lauren, a bicycle propelled my evolution: I didn’t enjoy getting grease on my pants as I rode about my neighborhood. Shorts became a necessity. And once I had them on, I felt better—looser, liberated even. Then came the pandemic, when a shirt with a collar felt like formalwear, and shorts no longer seemed quite so radical. And while I wouldn’t necessarily recommend wearing shorts for those who’ve RTO’ed (or wearing them on a dinner date to, say, The Polo Bar), I’m not not recommending them, either.

GETTING A LEG UP

From left, style icons including Pablo Picasso (© 2025 Estate of Pablo Picasso / Artists Rights Society (ARS), New York), Paul Newman, and Harrison Ford keep it short and sweet. Top, Ralph Fiennes donning pleated shorts in The English Patient.

There are a few key things to keep in mind. First, let’s start with the fabric. Anything designed for athletic endeavors should be reserved for, well, athletic endeavors. Instead, look to cotton, linen, even madras—anything a lightweight button-down might be made with. A rugged twill feels right. Corduroy is an unexpected option: A dash of campus style that can feel weathered from the first wear, in the best way. You could wear those for an easy hike, then straight to the post-exertion beer. Second, consider the details. Anything that takes its cues from full-length trousers can elevate a pair of shorts. Think of a coin pocket or a pleat. Add a belt in classic leather, rugged suede, or braided cotton for an easy upgrade. Look for an extended waistband or side tabs, or, like Mr. Fiennes or photographer Peter Beard, consider a Gurkha-style waistband. Or for a utilitarian look, consider the cargo short, a military-inspired option and longtime staple of Polo collections, not to mention what Mr. Newman is wearing for his beer run.

EASY BEING GREEN

A sophisticated mix of tailoring and utilitarian shorts from the Spring 2025 Runway Show.

Third, the fit. In general, you want something that hits the middle of your thigh. If you’re daring (and haven’t been skipping leg day during the winter), follow Mr. Glover’s example and go a little shorter. If you’re daring in another direction—the direction of statement style—consider the old-world appeal of a short that’s a little longer, maybe pleated, which offers the virtue of added sun protection for your legs. The trick is to look intentional, rather than going the full Bieber. Finally, it’s how you wear it. Fold up the cuff. Pair ’em with loafers. Consider a classic long-short move by wearing shorts with a long-sleeve oxford, or a sweater in cotton or cashmere. Take a cue from the Spring 2025 Runway Show and wear ’em with a navy double-breasted blazer, a preppy rebel look that feels timeless. Or make like Mr. Lauren and get creative—on that bike ride in Montauk, he’s actually not wearing shorts, but chinos he transformed into shorts the old-fashioned way: with a pair of scissors. A cut above indeed.

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