Complimenting, NFL Anchors, and Suit in a Box: Pocket Squares, Winged Puff Fold, Day 2

“Hey, I really like your…pocket…silk…handkerchief-thingy.”

When I first started rocking the squares, I got this a lot. No one knew what to call them. Either because of their increased popularity, or my proximity to the fashion Mecca of NYC, I get this less today.

Nonetheless, whether the person fumbled with the name, I appreciated the compliment. More than that, I appreciated that my clothing was able to break that invisible barrier that lies between strangers. In a world full of distractions, something that can lead to spontaneous human interaction is a precious commodity. Sometimes, it led to a conversation. Othertimes, it was a simple remark in passing. What was certain was that the compliment brightened my day.

Which brings me to the topic of matching versus complimenting.

A complimenting pocket square speaks to your overall outfit. It may pick up a subtle color of your suit, shirt or tie, or otherwise be a complimentary color to the main color that your outfit is projecting. If you are not sure what complimentary colors are, they are those that are directly across from each other on the color wheel.

Color matching, advanced color and pattern matching is a topic for another post. A more important topic should be discussed at the beginning of this journey into the land of pocket squares, if only to be avoided.

There exists in America a bastion of pocket square purgatory: NFL Sunday. Perhaps this is where many people are used to seeing pocket squares on a regular basis. But do not let these men be your guides in the land of kerchiefs. They may know the X’s and O’s of football, but for the most part, their command of style is not fantastic.

Thank you Howie for being the one guy who didn’t buy his pocket square with his tie. Bad Jimmy Johnson.

The reason why having an exactly matching pocket square and tie is a no-no has to do with yesterday’s post. It’s about caring. And wearing a pocket square that exactly matches your tie to your pocket square is just…kind of lazy. And pretty uninteresting. It also looks like you just went to the store and bought this:

There is an argument to be made that this “rule” is tied to elitism. Your high end men’s brands don’t sell shirts, ties, pocket squares, tie bars, and cufflinks that all match in a single box. Some people would say that no one should sell something like that. Ever. However, don’t let the price tag of that suit in a box versus the retail price of individual ties, shirts, pocket squares, and other accessories dissuade you. Know what you are looking for and shop the sales. You will more than likely find all of those things in a higher quality and for less than the retail price of the suit-in-a-box atrocity. Like I said, it’s about not being lazy.

The final word that I will say is that a tie and pocket square of the same material is basically like a Canadian Tuxedo for actual suits.

So what do you do? Pick a pocket square that matches or compliments your shirt, or matches a minor color in your tie. The pocket square serves to break up the line of the jacket, and adds interesting color and texture of the outfit. Don’t be afraid to wear a pocket square of a different fabric than your tie.

Today’s fold is a fairly simple, but versatile one. The Winged Puff. It tends to be more formal, but can be worn somewhat dressed down as well. It is also very simple to do, and can be done with nearly any fabric or size of pocket square.

1. Start with your pocket square


2. Then fold diagonally in half.


3. Take the corners and fold them to the bottom center corner of the pocket square.


4. Fold the edges of the pocket square in to the width of the pocket that you will be inserting it into. Smaller pocket squares will require less of this tucking.


5. Fold up the bottom to close and lock the fold, and it’s ready to go in your pocket!


6. Viola! There you have it. Don’t be afraid to pull at the side of the wings to adjust the size and width of the peak at the top.


This is also one of my favorite (bow) tie pocket square combos. The floral pattern has a tiny tiny bit of yellow in it, but the fact that it’s a floral pattern just makes the yellow fit that much more. Happy folding everyone. Any questions, feel free to email me at

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