Men Wear Short Shorts. And Long Shorts. And Everything in Between.

Nickelson Wooster, a fashion consultant and a frequent subject of street style photographers, is known, among other things, for his taste in shorts. He wears them long and short, loose and tight, in leather, wool and twill.

“Shorts are like skirts, and I think any woman will tell you there is no one length or shape that fits every single person,” said Mr. Wooster, 63, who goes by Nick.

On the surface, it might seem like shorts suffer from a case of nominative determinism — their name tries to tell us what to expect from their appearance. In practice, the length of shorts can vary wildly. They can reach down to the top of the shins or stop a few inches from the hip.

Still, every few years, the same question surfaces: How short should they be?

Recently, thanks in part to widely circulated photos of the actor Paul Mescal in thigh-baring shorts, there’s a clear answer: pretty short.

Ross Figlerski, 32, recently started leaning into truncated inseams. “I’m a bigger guy, and I find them a lot more flattering and reliable for whatever outfit I end up wearing,” said Mr. Figlerski, who lives in Brooklyn.