I've had it. While the problem doesn't arise with more casual attire, I am terribly frustrated by the fact that most of my watches are too large to wear when I put on a dress shirt with suit and tie. I'm forced to pass on my favorites, Siffert and Speedy, as they just don't fit comfortably, if at all. Rolex is barely doable, and I frankly don't care much for it and feel pretentious with it on.
Granted, I can get an entire new custom shirt wardrobe with cuffs enlarged to fit my watches, but that would eat into my watch budget. It's not that I'm complaining (too much), but rather venting my frustration at being denied my ability to wear whatever watch strikes my fancy on any given day.
Scott