Pocket Square Chicago

Explore PocketSquares Across Chicago — A Dive Into Fashion Culture Over Time


PocketSquares can take on a life of their own — bringing a certain color, tone, or “feel” to an outfit for any occasion. One may wonder exactly how to style this classic fashion accessory, pulling inspiration from the rich archives of Chicago fashion history. 

If that’s you, you’re in the right place! 

Read on to learn more about the many different styles and accessories PocketSquares offers. From pocket square organizers in Chicago to everything you need to know to make your pocket square experience uniquely distinctive. 

Wedding Pocket Square With That Distinctive Chicago Flare

Perhaps one of the most famous models of the pocket square is showcased in wedding attire. Our residents know how to show up and show out for their favorite events.

We’ve seen pocket squares worn with Chicago style for centuries, and it’s clear why. No one can argue the elegance that a pocket square brings to an outfit, offering both a practical and a stylish accessory to groups large and small. It fuses looks, complements a style, and will accessorize seamlessly, drawing the eye to the wearer’s face and unique features. 

Classic Midwestern Pocket Square Use 

Many historians concur that the pocket square rose to fame in the 14th century, signifying wealth and a level of social class. While you wouldn’t necessarily expect to see pocket squares on a farm in the mid-1800s midwestern world, they were commonly used for special events to denote elegance and class an event might demand — such as going into town, to church, or for other social functions. 

In this use, they offered a muted signal of respect and taste despite many wearers opting for more practical styles (such as the plain white variation or classic handkerchief). 

Avant Garde Fashion Square Wear 

With a recent acclivity in the trend over the past few years (and a particularly dominating spike in the early aughts), avant-garde fashion favors brighter, bolder, and unorthodox designs and styles. In this context, people might wear their squares in a way that sends a message, inspires, or provides a glimpse into one’s more unusual or unique fashion tastes. In either case, it’s a win and another example of how fashion can serve as a communication medium. 


Define Your Fashion Sense With SquareGuard!

Considering making a pocket square a part of your daily ensemble? The team at PockeSquare is here to help. We’re committed to unearthing your style and guiding you to the perfect square, capturing your unique essence and fashion sense. For more information and to get started today, please contact us online. We’re here to help.

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