Don’t Worry About Your Pocket Square

When guys decide they want to up their style game, or simply want to start dressing “better” (whatever that may mean for them), one of the first steps is experimenting with pocket squares.

And I think that’s great! Pocket squares are an easy, inexpensive way to take your style game up a notch.

You already know the basics regarding pocket squares. Make sure they don’t exactly match your tie. A white, linen square always looks good.

But once you start wearing pocket squares, you might feel a little self-conscious if your square isn’t “just right”. If it’s not folded properly, or if too much or too little is showing. After all, the details are important, aren’t they?

This can lead you to feeling not-quite-your-best, especially after a long day where your pocket square is bound to move around. But what’s the solution? Do you adjust it every so often throughout the day? Do you glance at it in the mirror of the men’s room and stuff it back into place?

This is a common conundrum among well-dressed men since we naturally have an eye for detail. There are also certain “ideals” (for lack of a better term) when it comes to certain aspects of menswear, like how much shirt cuff should show beneath the jacket sleeve or how much break the hem of your trousers should have.

We tend to apply this to pocket squares. We put our squares in the perfect placement in the morning when we get dressed and trust they’ll stay constant throughout the day the same way our shift cuffs do. Unfortunately, pocket squares shift position as we move around, which means they are NOT going to look the same at 3pm as they did at 7am.

I am here to tell you that that’s OK!

Don’t worry about the appearance of your pocket square. A pocket square’s appearance should be on the same level of consideration as a bow-tie knot. Meaning you should adjust it as you want in the morning but then accept that its appearance will change throughout the day. That’s ok and you shouldn’t get bent out of shape about it.

Here’s why you shouldn’t worry about it…

The time period that we clothing enthusiasts often point to as the “Golden Age” of menswear is from the 1930s to the early 1960s. Think Cary Grant to young Paul Newman. This is the time we look to for our style standards. If you look at how these men wore their pocket squares, you’ll see everything from giant plumes to slim, white slivers.

Clark Gable, who was one of the best dressed men of all time, regularly had his pocket square spilling out of his breast pocket (as did many of his costars).

Humphrey Bogart often went with a smaller, more understated square.

Gregory Peck often sported no square at all.

These men simply stuffed a square into their pockets (if they wore one at all) and got on with life. There wasn’t much thought given to how it looked. And I think we can all agree that no matter how much square was showing, they looked great!

So, please don’t think that you appear poorly-dressed if your pocket square is a little askew. You look great and you should feel confident!

But, if the placement of your pocket square is something that genuinely causes you grief, here are a few tips for keeping it in place.

First, the material of your pocket square makes a big difference. A linen square is great since linen is a pretty rough material. Since it’s a little scratchy, it’s not going to slide around all that much once it’s in your pocket, especially if you’re wearing a textured jacket like a tweed.

On the other hand, if you have a 100% silk square, there’s more of a chance that it will shift position as you move. Coupled with a smoother textured jacket like the worsted wool of your suits, and you can see why your squares don’t sit still.

I recommend either a linen square or a square that’s made from a silk and wool blend. I have a few squares from Poszetka and they are a lovely blended fabric which gives the square a touch of roughness. These squares don’t really budge too much while sitting in my pocket all day.

Second, consider the size of your square. A larger square, especially if it’s a smooth silk, is going to ooze out of your pocket over time. A smaller square won’t do that, as much. I have a cream-colored square from Brooks Brothers that I love which goes great with my tweeds, but it’s so big that my pocket practically regurgitates it after only a few minutes of wear. I wish it were a smidge smaller so it stayed in place better.

Then, there are instances in which you might not wear a square at all! And that’s ok, too. If your jacket sports a busy pattern, like a madras or tartan plaid, the addition of a square might be a bit too much, visually. Also, if you are using your jacket purely for outerwear purposes (like a thick tweed) then a square might feel a little dandyish. In those circumstances feel free to eschew the square entirely and don’t give it a second thought.

In your menswear journey there are things you SHOULD worry about and things you SHOULDN’T worry about. Exactly how your pocket square looks falls into the latter category.