Here at Kempt HQ, we often receive letters from our readers—most of it adoring fan mail, but every so often we get a nude photo. Also every so often, we get an inquiry from a wayward soul that we feel compelled to answer…

“Pocket squares. I have them. I also have blazers. I want to wear pocket squares in my blazers. But not all squares are sized alike, and neither are all pockets. What should I be looking for? I have a pile of unused squares in a drawer, yearning to be free.”

While it sounds like a simple sizing issue, this conundrum goes a lot deeper, centering on how one approaches the philosophy of the pocket square. So, dear reader, we’ve come up with a six-step plan to put you on the path to pocket-square enlightenment.

It might take you a few tries to get it right: Some squares work better with certain jackets—whether it’s the size of the pocket, the material or colors. The only way to really understand what works together is giving it a go. If by midday the square has disappeared into the depths of your pocket after many attempts to resize it so it stays up, that’s not a good match.

Don’t fuss over it… for too long: The tendency with something as delicate as a square foot of silk or linen is to be extra gentle—especially since they come so neatly folded. But these things can take a good amount of creasing and bunching up.

Don’t be afraid to get a little creative: We have it on high authority that chopsticks can do wonders when coaxing a square down a particularly deep breast pocket. We’ve also heard rumors of dapper gents folding a tissue in first, to keep the square flying high.

When all else fails, just stuff one into your pocket and head out: The driving force behind any sartorial flourish is to embellish your general flair while not looking like you tried too hard. There’s nothing wrong with taking that to heart.

If it’s not broken… When you finally manage to get a particular square just-so in a favorite blazer, don’t be afraid to just leave it in there.

Or just skip it: We’re usually of the mind that a pocket square is never a bad idea, but if you’re feeling hassled, just skip it. We’re confident you’ll make up for it somewhere else.

—N.B.

CONTRIBUTORS

  • Najib Benouar