I have mentioned the great value of a lowered second button on an OCBD multiple times before. We all know the old six button fronts had the second button lower than modern shirts due to modern shirts most often being seven button fronts. The question however is exactly how much lower was the second button? How far do I need to lower my second button to get the same look?
Notice the photo at the top of this piece. It is a photo of a 1980s six button front Brooks Brothers OCBD. Notice how low the second button is. Notice how relaxed it appears with only one button undone. In this piece I am going to give the exact measurements of this shirt as it pertains to the second button in comparison with a newer seven button front Brooks Brothers traditional fit shirt.
The photo above is a comparison of the 1980s Brooks Brothers six button front on the left and the newer seven button front Brooks Brothers traditional fit on the right. Notice it is a substantial difference.
The photo above is the same comparison, but with a tape measure included so you can see the exact measurement. Notice that on the newer shirt, the bottom of the second button hole is just above 3.75 inches from the first button hole. Notice on the 1980s six button front the bottom of the second button hole is just about 5 inches from the first button hole. This is a 1.25 inch difference. It may not seem like a lot, but it is a lot. That 1.25 inches does a lot of work and it makes a massive difference.
If you want to create this classic look by way of custom shirt, you will want to tell the maker that you want the bottom of the second button hole to be 5 inches from the first button hole. That is the key. If you can get that, you can create essentially that same relaxed breezy look on a seven button front shirt.