I've worn a Tiffany's watch for 7 years now and I'm still quite fond of it. Like some of the other above posters, I had a hard time finding the right size and the Tiffany's watch I chose is perfect. I've had no issues with it (knock on wood) and it's aged very well.
I like having something a little different and not cliché like, say, a Rolex. If I ever "upgrade" I'll go Cartier most likely but there's no rush, this watch has been a great piece.