Pocket Square Strategy

Sometimes it’s the smallest things that make the biggest difference and the pocket square just so happens to be one of those things. Whether it’s playing a subtle, supporting role or adding a punch of color or pattern that elevates your entire look, the right pocket square choice is going to finish off your suit or blazer in just the right way. Just like The Dude’s rug, a pocket square is going to tie everything together, but it’s not as simple as just grabbing one and throwing it in your chest pocket. As you’re going to make your pocket square choice, you want to consider a few simple pieces strategy in order to make the right choice.

Before you start, consider the season and material...

Sure, a silk pocket square always works, but as with any suit you were throughout the year, a next level accessory addition that is season-specific can bring the whole look together. If you're wearing summer suits in alternative fabrics like cotton and linen, you can mirror this fabric choice with your pocket square. The look, feel, and texture of a cotton or linen pocket square will continue the vibe set by your suit in a nice way and the limited contrast of a less formal fabric will complete the package nicely.

Now let's talk beginner, intermediate, and advanced strategy.

Beginner - Keep It Basic With White
If you’re a pocket square rookie it’s easy to start simple, and a crisp white square (ironed, if necessary) tucked into a neat fold is the perfect place to start. The best thing about going with white is that it’s foolproof. It’s going to match seamlessly with every type of suit and color combo and looks especially great with a tux. So if you’re looking for a subtle finishing touch, start here. With a suit, silk or cotton works but if you’re going to wear one with a tux, the formality demands one in silk.

Intermediate - Complement With Color or Pattern
Now that you’ve got the basics down and you’re ready to step up the intermediate level, it’s to think about adding some color and subtle pattern to your square. First, it's important to look at your suit color combination and choose a square in a complementing color. Pick one color that’s in your suit, shirt, or tie and have that be the primary color of the pocket square. You never want match identically, but you don’t want to throw in something random either. From there, if you want to add some pattern, start with something subtle like a simple stripe, small geometric pattern, or a paisley. Keep the scale of the pattern small to start, especially if you’ve got any additional pattern in your tie or suit.

Advanced - Go Bold and Make a Statement
Now it’s time for your black belt style test, let’s do this. Since you’ve mastered the different ways you can bring the pocket square into your rotation, let’s use it as a statement piece. Obviously it’s important to consider the occasion, and this move is probably not the way to go if you’re working in conservative or formal office environment. But, if you’ve got event, wedding or work in a casual office environment, let’s swing for the fences. As we did last time around, you want to keep one complementing color going but choosing something with bolder, brighter punches of color to contrast is going to take you to next-level status. In terms of pattern, if you’re going with a large-scale print or paisley in your pocket square, have that be the focal point of your look. Don’t try and compete with other large-scale patterns or bright colors in your tie or blazer, it’s going to be way too much to handle and you’re going to end up looking like “that guy” and not “that super-stylish guy”.