I still remember the first time I held a pair of cufflinks. I had no idea what to do with them. If you feel the same, you are not alone.
Learning how to wear cufflinks can feel confusing at first, but it is actually very simple once you know the steps.
In this article, I will walk you through everything from the right shirts to wear them with, to styling tips for different occasions.
I have helped many beginners get this right, and I am confident you will too.
What Are Cufflinks and How Do They Work?

A cufflink has two main parts: the face and the backing. The face is the decorative side you see on the outside of your cuff. The backing holds it all in place from the inside.
Together, they clamp through the buttonholes on your shirt cuff, replacing the standard button. Different cufflinks close in different ways.
The most common types are bullet back, whale back, fixed back, chain link, silk knot, and locking closures. Bullet and whale back styles flip to lock in place.
Chain links are classic and formal. Silk knots are casual and colorful. Each style works a little differently but serves the same purpose.
Shirts That Work with Cufflinks
Not every shirt works with cufflinks. Here is what you need to know before buying one.
French Cuff Shirts

French cuff shirts are the most popular choice. These shirts have extra-long cuffs that fold back on themselves. They have four buttonholes instead of one.
Cufflinks are not optional here; they are required to close the cuff. If you are new to cufflinks, start with a French cuff shirt.
Tuxedo Shirts

Tuxedo shirts are made for formal events like black tie dinners or galas. They usually come with front plackets and stiff bib fronts.
Cufflinks here should be simple and formal. Think silver, gold, or onyx. Keep it clean and minimal.
Convertible Cuffs

Convertible cuffs are great for beginners. They have both a standard button and a buttonhole for cufflinks. You can wear them with or without cufflinks.
This gives you more flexibility depending on the occasion.
Shirts to Avoid

Do not try to wear cufflinks with barrel cuff shirts. These are your regular everyday shirts with a single button sewn into the fabric.
There is no buttonhole on the outer side, so cufflinks simply will not work. Casual shirts like flannel or linen button-downs are also not the right fit.
How to Wear Cufflinks Step-by-Step Guide
A simple guide to wearing cufflinks correctly, from choosing the right shirt to styling them for any occasion.
Step 1: Unbutton and Prepare the Cuffs

Start by unbuttoning the cuffs of your French cuff shirt completely. Let both layers of the cuff hang loose and open.
Step 2: Fold and Align the Cuffs Properly

Fold the cuff back on itself so the two layers line up evenly. The inside of the cuff should face outward. Make sure the fabric is flat with no bunching or twisting.
Step 3: Position the Cufflink Closure

Hold your cufflink with the face pointing outward and the backing flipped open. If it is a bullet back or whale back, make sure the toggle is rotated to a straight position so it can pass through the holes.
Step 4: Insert the Cufflink Through Holes

Line up all four buttonholes (two from each layer of the folded cuff). Push the post of the cufflink straight through all four holes at once. This keeps the cuff closed neatly.
Step 5: Secure and Adjust for Comfort

Once the post is through, flip the toggle or backing to the locked position. Give it a gentle tug to make sure it holds.
The face should sit flat on the outside. Adjust the cuff so it sits about half an inch below your jacket sleeve.
How to Style Cufflinks for Different Occasions

Cufflinks work for many settings. The key is matching them to the mood of the event.
Formal Events (Black Tie and Weddings)
Go for simple and refined. Silver or gold cufflinks with a plain face work best. Avoid anything flashy or colorful. Round or square shapes in metal are always a safe choice for black tie.
Business and Office Wear
For office settings, keep it professional but not too stiff. Navy enamel, brushed silver, or simple geometric shapes work well. Match them loosely with your tie or watch for a polished look.
Semi-Formal and Social Events
This is where you can have a little more fun. Try novelty designs, colored stones, or interesting textures. A dinner with friends or a cocktail party gives you room to show some personality.
Casual Styling with Cufflinks
Silk knots are your best friend here. They come in many colors and work well with a relaxed convertible cuff shirt. Pair with chinos and a blazer for a smart casual outfit that still looks put-together.
Tips for Wearing Cufflinks the Right Way
Small details make a big difference. These tips will help you wear cufflinks with confidence.
- The silver watch goes with silver cufflinks. Gold watch pairs with gold or warm-toned cufflinks. Keep metals consistent.
- Let the occasion guide your cufflink style. Metal for formal, enamel or novelty for casual and semi-formal settings.
- Your shirt cuff should show about half an inch past your jacket sleeve so the cufflink face is visible.
- Do not hide your cuffs inside your jacket. If they are not seen, the cufflinks lose their purpose.
- If you are wearing a watch, tie bar, and pocket square together, make sure everything works as one look, not against each other.
- Cufflinks are one piece of the outfit. Keep the rest simple so they stand out without looking overdone.
Conclusion
Learning how to wear cufflinks changed how I think about dressing up. It is one small detail that adds a lot. Once I got the hang of it, I started reaching for cufflinks every chance I got.
They are simple, timeless, and work for so many occasions. If you have been holding off, now is a good time to try them. Start with a French cuff shirt and a basic pair.
You will be surprised how much confidence a small thing can bring. Drop a comment below and let me know how it goes.
Frequently Asked Questions
Can I wear cufflinks with a regular shirt?
No, regular shirts with sewn-in buttons do not have the right buttonholes. You need a French cuff, tuxedo, or convertible cuff shirt to wear cufflinks properly.
Are cufflinks only for formal occasions?
Not at all. Silk knot cufflinks and fun enamel styles work great for casual and semi-formal settings. Cufflinks fit many dress codes depending on the style you pick.
How do I keep cufflinks from falling out?
Make sure the backing is fully locked after inserting. Bullet back and whale back styles are the most secure. Always do a gentle tug test before heading out.
What size cufflinks should I wear?
Most standard cufflinks are between 16mm and 20mm in diameter. Larger faces suit bigger builds and bolder looks. Smaller faces are better for formal or minimalist outfits.
Can beginners wear cufflinks without looking overdressed?
Yes, absolutely. Start with simple silver or brushed metal cufflinks on a business shirt. Keep the rest of your outfit clean and simple. You will look sharp without going overboard.





