Nothing is more frustrating that wanting to wear a specific watch and you can’t because it doesn’t fit under your shirt cuff. Here are some simple how to instructions to modify the button to give some room for larger watches. It is not difficult and like everything else gets easier with practice.
Tools:
Needle, thread and something to cut the thread with.

Shirt.

Step 1.
Thread your needle with about 2 arm spans of thread. More is better. Thread is cheap. Locate the needle in the middle of the thread and fold the thread in half and tie several knots at the end. The knots will anchor the thread in the shirt.

Step 2.
Remove the existing button. Pretty simple.

Step 3.
OK, this is where it gets difficult. Basically we are going to reattach the button, but instead of putting it right against the shirt, we are going to extend the length of thread connecting the button to the cuff. Use something to act as a spacer. Here I am using a marker pen that will give 2-3 cm in length between the button and the cuff.
First poke the needle through the underside of the cuff and pull all the way through. You can use the same holes from the original button setting. Then thread the needle through one of the button holes. Place your spacer against the cuff over the intended location of the button. Slide the button all the way down to the spacer. Poke the needle through the opposite button hole, put it around the spacer and then poke through the cuff to the underside. Pull tight to help secure.

Now push the needle again through the underside of the cuff, go around the outside of the spacer and put through a new button hole. Cross over to the opposite button hole and then go around the spacer again and then push through the shirt cuff.

Repeat this process a whole bunch of times. I would guess 10-15 times. Continue until there is a mass of thread similar to what is on the original button. With each pass it will get easier because things will be more secure.
Step 4
When you decide that you have done enough you want to end with the thread through the button, but not pushed through the cuff. You want the needle and thread on the same side as the button. Pull the spacer out and it will look like this.

Now this is where it all comes together. You have this mess of thread that you are going to secure by wrapping the thread around and tie off in several spots. I believe this is called a shanked button, so I will call it that. First make a simple knot at the top of the shank right under the button. Give the button a few twists just to tighten up the loose threads.

Then start wrapping/winding the thread around the shank in a spiral fashion. The more the better, working your way down toward the cuff. When you get ½ way, tie off a simple knot just to secure what you have done. Continue on to the bottom of the shank and tie off again. Push the needle through the bottom. You should have something that looks like this.


Step 5
Now with the needle underneath the cuff, loop it through one of the threads and make a knot. Repeat this 3-4 times to tie off the thread. Cut the thread off and you are finished. Here’s a picture of the finished product.

And here is a demonstration with the largest watch I have. The case is 15 mm thick and fits easily under this cuff.


So I did this to a couple of shirts several months ago as pilots. My shirts are laundered and pressed at the cleaners and the buttons have held up fine. I think when it is buttoned, the extra thread is hardly noticeable, especially if you use a matching color to the shirt. One trade off is that when you are not wearing something thick like a quartz, the cuff will slip down farther on your hand than the other cuff.
Good luck!

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