How to use a pocket square without looking like you're trying too hard

You've got the suit. It fits well. The shoes are shined. But then you look in the mirror and something feels... empty. It’s that small, rectangular void on your left chest. Most guys panic here. They either grab a pre-folded polyester scrap that looks like a plastic fan or, worse, they try to match their tie perfectly. Don't do that. Honestly, learning how to use a pocket square is less about origami and more about understanding the "vibe" of your outfit.

It’s a tiny bit of fabric. That’s it. Yet, it carries this weirdly high stakes in men's fashion. If you get it right, you look like Cary Grant. If you get it wrong, you look like you’re heading to a high school prom in 2004.

The big mistake everyone makes with pocket squares

Let’s get the most important rule out of the way: Never, ever buy a matching tie and pocket square set. You’ve seen them in department stores. They come in a little clear box. They are a trap. Matching them perfectly looks cheap and unimaginative. It screams "I don't know what I'm doing so I let the manufacturer decide for me." Real style comes from coordination, not matching. If your tie has a hint of burgundy in the pattern, maybe your pocket square is a solid cream with a burgundy border. Or perhaps they share a similar texture but completely different colors.

Alan Flusser, the author of Dressing the Man and the guy who styled Michael Douglas in Wall Street, has been preaching this for decades. The pocket square should complement the shirt or tie, but it should always stand on its own. It's an independent variable.

Think of it like this: your tie and your pocket square are cousins, not twins. They should recognize each other at a family reunion, but they shouldn't be wearing the same outfit.

Why the fabric changes everything

Most people think a pocket square is just "a silk thing." Not true. The material dictates where you can wear it.

Silk is the classic choice. It’s shiny, it drapes beautifully, and it feels expensive. It’s perfect for weddings or formal galas. However, silk is slippery. If you try to do a crisp "TV fold" with silk, it’s going to slide down into your pocket before you’ve even finished your first cocktail.

Linen is the workhorse. If you are new to this, start here. White linen is the most versatile item a man can own. It stays in place because the fabric is "crunchy" and has grip. You can wear a white linen square with a navy blazer and jeans, or with a full tuxedo. It never looks out of place.

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Cotton is the casual brother. It’s similar to linen but usually a bit thicker. It’s great for work or a weekend lunch. Then you have wool and cashmere for the winter. These add a rugged, tactile depth to a heavy tweed jacket.

Mastering the folds (The ones you'll actually use)

You don’t need to know fifteen different ways to fold a piece of silk. You really only need three. Anything more than that and you're just showing off, and usually not in a good way.

The Presidential (or TV) Fold

This is the most formal and the easiest. It’s just a crisp horizontal line peeping out about half an inch above the pocket.

1. Fold the square in half.
2. Fold it again so it’s roughly the width of your pocket.
3. Fold the bottom up so the height matches the depth of your pocket.
4. Tuck it in.

That’s it. Don Draper made this famous. It works best with linen or cotton because they hold that sharp edge. If you try this with silk, it will look like a sad, deflated noodle.

The Puff Fold

This is for the silk enthusiasts. It’s supposed to look effortless, like you just shoved it in there and walked out the door (which is basically what you do).

1. Lay the square flat.
2. Pinch the center of the fabric and lift it up.
3. Use your other hand to form a "ring" around the hanging fabric and slide it down toward the corners.
4. Fold the bottom (the corners) up behind the puff.
5. Stuff it into your pocket and adjust the "pouf" until it looks right.

Don't overthink this one. If it looks too perfect, it looks fake. You want it to look a bit chaotic.

The Pointed Fold (The One-Point)

This is the middle ground. It’s professional but has a bit of flair.

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1. Fold the square diagonally to create a triangle.
2. Fold the two side corners inward toward the center.
3. Fold the bottom up.
4. Insert it so the single point is sticking out.

How to use a pocket square with different jacket types

Context is king. You wouldn't wear a neon paisley silk square to a funeral, and you wouldn't wear a stiff white linen TV fold to a creative tech conference.

If you’re wearing a double-breasted suit, keep the fold simple. The jacket itself is already a lot of "look" with all those buttons and wide lapels. A simple TV fold balances the drama.

For a sports coat or blazer, you can get weird. This is where you bring out the patterns—polka dots, geometric shapes, or even those crazy "scenic" prints where the square looks like a painting when unfolded. Since sports coats are inherently less formal, the puff fold is your best friend here.

Actually, here’s a pro tip: look at the edges. If your pocket square has hand-rolled edges (you’ll see a slight, uneven bumpiness at the border), show them off. That is a sign of quality. Machine-stitched edges are flat and boring; hand-rolled edges are a "secret handshake" among people who care about menswear.

Color Theory (Simple version)

Don't get bogged down in color wheels. Use your shirt as your anchor. If you're wearing a light blue shirt, a pocket square with some navy or orange (blue’s complement) will look great.

White is the "get out of jail free" card. If you are panicking and the Uber is two minutes away, grab a white square. It works with every single jacket and tie combination in existence. Period.

But what about the tie? If your tie is a solid color, go for a patterned pocket square. If your tie is heavily patterned (like a loud stripe or a floral), go for a solid pocket square. Balance is the goal. You don't want two patterns of the same scale competing for attention. If your tie has tiny dots, don't use a pocket square with tiny dots. Go for big paisleys or a solid color instead.

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The "Sink" Problem

Every guy has dealt with this: you put the square in, it looks great, and thirty minutes later it has disappeared into the bottom of your pocket.

If your pocket is too deep, you can stuff a bit of tissue paper at the bottom to act as a floor. Some people use a business card or a dedicated "pocket square holder," but honestly, a crumpled-up Kleenex works just as well and costs nothing.

Also, pay attention to the size. A lot of cheap pocket squares are too small (10x10 inches). These will always slide down. Look for squares that are at least 16x16 or 17x17 inches. That extra bulk keeps them wedged in place.

Why you should bother at all

It seems like a lot of work for a scrap of fabric. But in a world where everyone is wearing hoodies and tech-fleece, putting on a jacket with a pocket square says something. It says you paid attention.

It’s the most "low effort, high reward" move in a man's wardrobe. It takes ten seconds to put in, but it changes the entire silhouette of your torso. It draws the eye up toward your face and adds a layer of depth to your chest.

Actionable Steps for your next outfit

1. Audit your drawer. If you have those shiny, matching tie-and-square sets, donate them or separate them. Never wear them together again.
2. Buy one high-quality white linen square. This is your baseline. It should have hand-rolled edges.
3. Practice the Puff Fold. Do it five times in a row until you stop trying to make it look symmetrical. Symmetrical is the enemy of cool.
4. Check the scale. If you’re wearing a pinstripe suit, avoid a pocket square with thin lines. Go for a solid or a large-scale print.
5. Stop touching it. Once it’s in your pocket, leave it alone. Constant fidgeting makes you look nervous. If it slips a little, it just adds to the "sprezzatura"—that Italian concept of studied nonchalance.

The best way to figure out how to use a pocket square is to just start wearing one. Wear it to work. Wear it to dinner. Eventually, you’ll feel "naked" without it, and that’s when you know you’ve actually mastered it.