How to Wear Cufflinks: A Guide for First-Timers

Cufflinks are one of the few gifts that arrive with a prerequisite nobody mentions. A man opens a beautiful pair, looks at his shirts, and discovers the two things are incompatible.

This guide covers what you need, how to put them on, and when they are appropriate — written for someone who has never worn a pair.

First: do you have the right shirt?

This is the whole question, and it takes five seconds to answer. Look at the end of your shirt sleeve:

If everything in your wardrobe is a barrel cuff, you need one new shirt before the cufflinks are usable. That is not a failure of the gift — it is simply the order of operations.

How to put them on

Two pieces, four buttonholes, one direction that is correct.

1. Put the shirt on first, and do everything else — collar, buttons — before touching the cuffs. Fitting cufflinks to a shirt you are not wearing is far harder than it sounds.
2. Fold the cuff back on itself so the two halves meet. It should double over cleanly, ending roughly where a watch strap would sit.
3. Line up all four holes. The two sides of the cuff each have two, and they must sit directly on top of each other — not overlapping like a normal button cuff.
4. Push the cufflink through from the outside in, so the decorative face ends up on the outside of your wrist where people see it.
5. Turn the toggle flat. The bar on the back rotates; turning it parallel to your arm locks it and stops the link sliding out.

Two things people get wrong the first time: putting the face on the inside of the wrist, and folding the cuff around the wrist like a barrel cuff instead of back on itself. The fold is what makes the shape look right.

When cufflinks are appropriate

Cufflinks belong with a jacket. Without one, they read as fancy dress.

The rule that covers almost every situation: if you are wearing a jacket, cufflinks work. If you are not, they usually do not.

• Always appropriate — weddings, black tie, formal dinners, court, any occasion where you would wear a tie without thinking about it.
• Usually fine — client meetings, presentations, interviews at traditional firms. Keep the design plain.
• Depends on the office — in a business-casual workplace, cufflinks with no jacket can look like you are trying. Read the room before the first time.
• Skip — anything with rolled sleeves, and any setting where you are the only person in a jacket.

Matching, briefly

Match cufflinks to your metals, not to your clothes: whatever your watch and belt buckle are, silver or gold, follow that. Beyond this, plain designs go with everything and novelty designs go with almost nothing.

If they are engraved

Initials on the outer face; anything more personal belongs inside the box.

Engraved initials sit on the outward-facing side, which means they are visible when you reach across a table. That is the point — but it also means the engraving should be something you are comfortable having read at close range.

A useful division: initials or a monogram on the cufflink itself, and anything sentimental — a date, a line, a name — engraved inside the lid of the box instead. The first is worn; the second is kept. If you are choosing what to have engraved, our guide to engraving covers what survives being cut small.

Looking after them

The reason cufflinks disappear is that they have nowhere to live.

• Take them out before the shirt goes in the wash. The single most common way a pair is lost.
• Keep the pair together in one place. A box on the dresser beats a bowl of loose objects, because a single cufflink is worthless.
• Wipe metal with a dry cloth after wear. Skin oil is what dulls plating over time.
• Avoid the drawer-of-everything. Cufflinks get scratched by keys and coins faster than by wearing.

See engraved accessories  Preview an engraving free

Questions people ask

What kind of shirt do you need for cufflinks?

A shirt with double cuffs, also called French cuffs — an extra-long cuff with no buttons, designed to fold back on itself. Convertible cuffs, which have both a button and a buttonhole, also work. Standard barrel cuffs with buttons at the wrist do not.

Which way do cufflinks face?

The decorative face goes on the outside of the wrist, where it is visible when you reach across a table. Push the cufflink through from the outside in, then turn the toggle flat against your arm to lock it.

Can I wear cufflinks with a normal button cuff shirt?

No. A barrel cuff has only one buttonhole per side and is cut shorter, so there is nothing for the cufflink to pass through. Removing the buttons does not create the second buttonhole a cufflink needs.

Do you wear cufflinks without a jacket?

Generally not. Cufflinks read as correct alongside a jacket and as overdressed without one. In a business-casual office, wait until you have seen how others dress before wearing them jacketless.

Should cufflinks match your watch?

Match the metals rather than the clothes: if your watch and belt buckle are silver, choose silver-toned cufflinks. Plain designs work with everything.

Where should engraved initials go on cufflinks?

On the outward-facing side, since that is what others see. Keep anything sentimental — a date or a message — engraved inside the box lid instead of on the cufflink face.

How do you store cufflinks?

Keep the pair together in a dedicated box rather than a loose drawer, remove them before shirts are washed, and wipe the metal with a dry cloth after wear to stop skin oil dulling the finish.