Recently I did a post about Luciano Barbera and his watch over his shirt cuff. Several of the commenters thought it was just silly and affected but this is an example of why wearing a big watch over your cuff can be very practical.
I'm sure this gentleman's shirt sleeve length is perfect (this is the same gentleman, a tailor, that I posted recently looking supercool wearing a cream vest with his suit) but he will always look a little off when is sleeve is caught on watch.
Now, I'm not trying to get guys to start wearing their watches differently but I'm just saying it might not be as affected and maybe even more practical than not doing it.