To get the cogs whirring in your mind, let me tell you which watch I would pick from my own Rolex collection and why, then you can all tell me why I am wrong in the comments below. Okay. First of all, you need to think logically about such a painstaking request. If you are only allowed to wear one watch from today for the rest of your life, you are going to need a watch that will hold up in any type of situation.