I have decided to post this here after a fairly thorough search at TimeZone where I concluded that the average WIS wears his dressiest Phillipe Patek with open necked button down, sneakers, and jeans (these being the dressiest items in his wardrobe which lacks even in a "Californian tux" ). The context in which a watch is worn is seldom discussed in much detail. My question is this: What makes a dress watch "dressy" rather than "sporty"? Of course, there is, as usual, a hierarchy from dressiest to sportiest. Where does an officers dial face fit in? Arabic vs Roman numerals? Square vs round face? What effect do complications have on the dressiness of a watch? And what is your idea of the most formal dress watch?