So, you’ve finally ditched the plastic buttons for something with a bit more weight. Good move. But honestly, standing in front of a mirror five minutes before a wedding or a gala, wrestling with a piece of metal that refuses to cooperate is a rite of passage no one actually wants. Understanding how to put on a cufflink isn't just about the mechanics; it’s about not ruining your shirt or your mood before you even leave the house.
Most guys think it’s just "poke it through and hope for the best." It isn't.
The Shirt is the Secret Sauce
Before you even touch the jewelry, look at your sleeves. You cannot use cufflinks on a standard barrel cuff shirt—the kind with buttons already sewn on. You need a French cuff, also known as a double cuff. These are extra long and meant to be folded back on themselves. If you try to force a link through a single-button hole, you’re going to look like you're wearing an accordion on your wrist.
Line up the holes. That’s the first real step.
Fold the cuff back so the edges are even. You aren't overlapping them like a regular button shirt. Instead, you press the two open edges together flat. Think of it like a "kissing" cuff. The insides of the fabric should be touching each other. This creates a neat, stiff structural element that projects out from your wrist. It’s what gives that crisp, high-end look that Savile Row tailors like Richard Anderson or the experts at Turnbull & Asser have championed for decades.
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The Mechanics of How to Put on a Cufflink
There are a few different types of links, and they all behave differently. If you have the standard "bullet back" or "toggle" style, this is the easiest starting point.
- Flip the toggle so it’s parallel to the post. It should look like a little pill.
- Slide it through both layers of the cuff from the outside in. The decorative part—the face of the cufflink—should be on the "top" of your wrist when your arm is resting on a table.
- Once it’s through, flip the toggle back 90 degrees so it’s perpendicular to the post. That locks it in.
It sounds simple. In practice? You’re doing this one-handed. Most people find it easier to put the cufflinks on the shirt before they actually put the shirt on. Just slide your hand through the pre-linked cuff. It’s a pro move that prevents that awkward "teeth-pulling-the-fabric" maneuver everyone does when they’re in a rush.
Dealing with Whale Backs and Fixed Backs
Whale backs are similar to toggles but have a flat, solid "tail" that flips. They’re sturdy. Use them for work. Fixed backs, on the other hand, are a single solid piece of metal. No moving parts. These are the gold standard for elegance but a total pain to get through the holes. You have to wiggle the smaller end through at an angle. Think of it like threading a needle, but the needle is a piece of sterling silver and the thread is expensive sea island cotton.
Then you have chain links. These are old school. They have two decorative ends connected by a tiny chain. These are the most traditional and, frankly, the most "relaxed" looking because they allow the cuff a bit of movement. If you’re wearing a tuxedo, these are usually the preferred choice of style icons and vintage enthusiasts. They’re harder to put on because they don't provide a rigid post to push against, but the payoff is a much more sophisticated silhouette.
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Why Placement Matters More Than You Think
A common mistake is putting the decorative face on the wrong side. You want the world to see the "art," not the mechanism. When your arms are at your sides, the face of the link should be pointing outward. If you’re at a dinner table, the face should be visible to the person sitting across from you.
Don't overcomplicate it. Just remember: Inside to outside.
Material Science and Weight
Weight actually matters. Cheap, hollow cufflinks feel like nothing and often slip out of the holes if the fabric is soft. Solid silver, gold, or even high-quality stainless steel provides a "counterweight" to your sleeve. This keeps the cuff sitting where it should, right at the base of your thumb.
According to style historians, the cufflink gained massive popularity during the 19th century because starching techniques made shirt cuffs so stiff that buttons literally couldn't go through them. We don't use that much starch anymore, but the physics remains the same. A heavy link holds the shape of a modern, high-thread-count shirt much better than a flimsy one.
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The Silk Knot (The "Cousin" of the Link)
If you're at a semi-formal event and metal feels too "stiff," use silk knots. They’re called "monkey's fists" sometimes. They’re cheap, colorful, and much more casual. They work exactly the same way—you push one knot through the holes—but they offer zero flash. They’re great for a Friday in the office or a brunch where you still want to look like you tried.
Common Blunders to Avoid
- Mismatching metals: If your watch is silver, your cufflinks should probably be silver or a complementary cool tone. Don't mix a heavy gold link with a stainless steel diver watch unless you really know what you're doing.
- The "Button Overlap": Never try to overlap the cuff edges like a normal shirt. It creates a weird lump that ruins the line of your suit jacket.
- The Wrong Occasion: Cufflinks are for formal and semi-formal wear. Wearing them with jeans is a bold choice that usually fails unless you’re a rock star or a very specific type of European architect.
How to Put on a Cufflink: A Quick Summary of the "Kiss" Technique
Basically, remember the "Kiss."
You aren't wrapping the cuff around your wrist. You’re bringing the two ends together so they stand up. Hold them with one hand. Use the other to slide the post through. If you’re struggling, sit down. Use your lap to steady your arm. It's much easier than trying to do it while standing up and checking your reflection.
Once the link is through, give it a little tug. It shouldn't wiggle too much. If the hole is too big for the link, you might need a different shirt or a link with a larger toggle. There's nothing worse than losing a family heirloom because it slipped out while you were reaching for a drink.
Practical Steps for Your Next Event
If you’re heading out tonight, do this:
Check your shirt cuffs now. Ensure they are French cuffs. Pick your links based on your watch and belt buckle. If you’re using toggle links, flip the bar so it's straight. Fold the cuffs back perfectly—the crease should be sharp. Insert the links before you put the shirt on if you’re alone. It saves about ten minutes of frustration. If you’re already wearing the shirt, rest your wrist on a flat surface like a dresser to give yourself leverage. Push the link through the outside hole first, then the inner ones. Flip the toggle. You're done. Check the mirror to make sure the "good side" is facing out. Now, go grab your jacket and make sure about half an inch of that cuff is showing past the sleeve. That’s the "golden rule" of tailoring for a reason. It frames the hand and shows off the hardware you just spent time putting on.