Male jewelry is always a maze of conventions, but we recently ran across a particularly complex case via A Suitable Wardrobe: the pinkie ring.

A surprising number of well-dressed men have popped up wearing them, from Prince Charles to Jay-Z, so we understand a guy getting curious—but this is dangerous territory.

Like most affectations—a monocle, for instance—if you’ve got any doubt in your mind, don’t do it. It’s not a necessity. The success rate isn’t even all that high. If you know what’s good for you, you’ll take a walk right now, forget all this pinkie ring nonsense and go back to your easy, comfortable life of wingtips and oxford shirts.

But if you’re feeling stubborn, here’s how to make it work:

First, forget about Prince Charles. We know he’s a trad icon, but this isn’t a look for upscale Britons anymore, and it hasn’t been for some time. The icons here are Tony Soprano and De Niro in Casino. In a word, mobsters. When you see pinkie rings on guys like Sinatra, Jay-Z or, in more recent years, Rick Ross, that’s what they’re going for.

In moderation, it can be a pretty good look—especially if you’re a man of a certain age, trying to add swagger to a business suit. But as all those Casino suits should remind you, the look works best in extremely small doses. Ideally, you’ll want this to be the only piece of jewelry on your person (except possibly a wedding ring on the opposite hand). Even cufflinks could throw it off. Stay simple, and let that one chunk of metal be the only attention-grabbing point on your person.

As for the ring itself, keep it small and have a story behind it. Ideally, you got it from your grandfather or for saving someone’s life. Make something up if you have to, but have some tale at the ready before you wear it outside.

Maybe something involving a jaguar.

—R.B.

CONTRIBUTORS

  • Russell Brandom