You shouldn't wear it, because you don't seem to be confident enough to wear it. I can imagine that if someone (a client/business partner) would ask you how can you afford a Rolex, you would get red in the face and wouldn't be able to justify it (just my two cents based on what's posted above).
You should wear it because you like it and you can afford it and not because of showing off. It's like with expensive cars, there are people who's buying BMWs and they look totally naturally with the car and on the other hand, there are people with BMWs when you look at them, you see the car is totally out of their league and they're just trying to show off, but it has the exactly opposite effect (aka fake Rolex).
IMO, don't showoff when meeting a sick person, when visiting poor, and on a funeral... Other times, it's your own funeral as the saying goes (not literally ofc), let there be a grand scale with rock band playing, and go out in style, or not..... Who cares? Jk 
