It’s Christmas Eve. That means at some point in the next 24 hours you might be faced with the opportunity to don a fur-lined topper, Santa-style…

Now, we included the Santa hat in our holiday must-haves, but with a stern disclaimer: there’s a time and a place for taking such a sartorial risk. If that time’s ever going to come, it’s tonight.

So in the event that you’re feeling up to the challenge, we’ve found some of history’s most stylish gents pulling off the look—from Bing Crosby to Ryan Gosling—and put them here for you, sort of as a sartorial confidence booster. (And as something to keep you occupied for the next couple days, until Kempt returns to our regularly scheduled dapperness.)

Presenting: the art of wearing a Santa hat, according to the style gods…

—N.B.

CONTRIBUTORS

  • Najib Benouar