I can't say I am a huge watch person, though if you were to see how many I have you might scoff at that and suggest I rethink that position. Realistically though, I have two functional watches, a bunch that I just haven't bothered to throw away and a single watch that I keep for sentimental reasons. In my family, when you turn 13 you receive your first "nice" watch. It is a right of passage kind of thing I guess, so I keep that watch, even though it no longer tells the time (it probably would if I got a new battery for it etc). I have my work watch which is the one that is on my wrist 99% of the time. It is a G Shock World Time, so I am able to set the digital world timer on it to Nebraska (though I have to actually set it to Chicago for that specific time zone) in order to know what time it is for conversations that I have with VIPs. It also has a bunch of other functional aspects that are pretty handy with my work and just personal things like PT. My third watch is a nice one (though for the life of me the brand escapes me at the moment). It has diamontees around the face and a nice black band. It is what you would call a "nice" or "dress" watch. I wear it occasionally when I am going out somewhere nice.
It's funny - I have three watches that are of any great importance to me, and yet I have friends who collect watches so as to co-ordinate with their outfits. They have a half dozen fancy pants watches as well as functional day time watches. Surely - given you only have two arms and therefore two wrists one single person does not need in excess of 10 watches?!?!
But hey...not my money.
I have one that I keep because its important, and two that tell me the time (one slightly nicer than the other). That'll do I think.