I had to keep digging.
In general, many folks were in favor of night shorts—with some stipulations.
Outspoken on the pro-shorts side is Chris Black, co-host of the menswear-centric podcast How Long Gone and a sometime contributor to GQ, who thinks shorts are “appropriate most of the time,” give or take at certain upscale restaurants. “First and foremost, I don’t give a shit. If it’s hot outside, I have to prioritize my comfort,” Black said by phone while vacationing in Italy, where he’d been wearing lots of shorts. “Also, if I’m being completely honest, I think that the only good part of my body is my legs, [and] I’m happy for them to be out there.” He does have his shorts specifications: they can be baggy, flowy, athletic or khaki, but wear them with loafers (penny, Belgian, or “something a little more upmarket”), skip the socks, and go for a collared shirt or a crewneck sweater; T-shirts and sneakers with shorts are for daytime.
Rainer Castillo, co-founder of the robustly pro-shorts shorts company Chubbies, who was married in shorts and a blazer, admitted he’s “obviously biased on this particular topic.”
He has his reasons. “The pandemic over-casualized us and brought the equilibrium more in favor of casual, and I think as a result you’re going to find a lot of men wearing shorts in places they haven’t in the past,” said Castillo, speaking recently via Zoom from Austin, Texas, where he, and Chubbies, are based. “I think this is also regional—the idea of wearing pants out on a date in Austin isn’t an option. It’s like, good luck, it’s too hot, you’re gonna burn up in July,” he noted, before making another good point: “New York has its own… They have a lot of rules in New York. And I think the rest of the world’s looser.”
GQ style editor Yang-Yi Goh, meanwhile gave a considered green light: “Follow the same dress code standards that you would otherwise apply to pants. If you’re going to a wedding, for instance, maybe skip the nylon Baggies in favor of some dressy linen shorts that’ll look good with a blazer.” Meanwhile, GQ commerce writer Gerald Ortiz advised that “if the occasion leans dressy but it’s an outdoor situation (say, a night-time garden party with your bougie buds), then a roomy pair of wool dress trousers could fly.” But apart from that? “If it’s too damn hot, then I’m wearing shorts any time, anywhere.”
As far as no-go occasions, Goh said it’s safe to say you shouldn’t wear shorts to a wake or a funeral—“anywhere where the focus shouldn’t be on you, which, if you’re wearing shorts at night to an otherwise formal event, it *will* be.” Ortiz’s fellow commerce writer Avidan Grossman concurred: “Shiva. Do not wear shorts to a shiva.”
The designer Thom Browne is, unsurprisingly, pro-shorts, if only because he is staunchly pro-do whatever you want. In an email, Mr. Browne offered a simple decree, punctuated with his signature typographic ellipses: