I don't get the whole watch thing. I wear a $40 Timex that I think looks good and works as well as a $250k diamond encrusted Rolex. Wearing an attention getting watch would not feel right to me.
That said, I've admired Rolexes on other people's wrists. It's like other jewelry or even tattoos, I can like something on someone else but not on myself. Also, when it comes to cars/houses/clothes/music/taste in women/etc., just because I don't share it doesn't mean it's wrong. What's the point of freedom if you can't wear what you like?