Letters from the Old World

Letters from the Old World

The Most Revealing Detail in Menswear

And what it says about you

Evan Amato's avatar
Evan Amato
Mar 27, 2026
∙ Paid
Original photos by Raphael Barberi.

Style is fundamentally about two things: the big picture, and the small details.

The big picture is composed of things like fit and proportion. You can wear the most expensive suit in the world, but if its cut isn’t flattering, you’ll never look good in it. On the other hand, if you know the fundamentals of proportion, you’ll look good no matter what you wear.

As for the details, these are the things that make your style look authentic and lived in. These include everything from the way your suspenders attach to your trousers to the type of leather your shoes are made of. Once you master the big picture items, the details are what bring your look to life.

Most people go wrong by focusing on everything in the middle. They watch James Bond or Peaky Blinders and think that if they only get the right suit or the right tweed jacket, they’ll look just as cool as the protagonists. But if you’ve been reading our weekly What’s In a Fit articles, you’ll know why this never works.

So far in this series, we’ve covered big picture items such as color, contrast, fit, and how to not look like you’re LARPing. We’ve covered details in articles about pattern mixing and dressing like the landed gentry. Today, however, we tackle what is perhaps the most overlooked, yet most revealing detail in menswear: the pocket square.

Hand-rolled edges reflect the artisan’s attention to detail.

The story of the pocket square is a fascinating one. Starting with its humble origins as a literal snot rag, it has since come to be the one item of menswear that reveals more about its wearer than perhaps any other. But how did it come to symbolize so much? How do you wear one, and what does how you wear it reveal about you?

Today, we look at the underestimated power of the pocket square. We’ll discover why it has such a powerful visual effect, share practical examples of how to style one with different colors and fabrics, and explore what it reveals about its wearer’s character and philosophy.

Who knew there was so much to explore in one small piece of fabric? Now, let’s dive in…

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