Most of us with collections of more than a couple watches have some that are more expensive than others. Do you wear these watches more or less than the less expensive ones?
I'm fortunate enough to have 3 watches that cost >$2K (new), 2 Rolexes and 1 Omega, but I rarely wear them. My rationale is that I don't want them to get damaged. Not the most sound reasoning considering they're just metal and basically really hard glass (hesalite for Speedy), but I just can't put them when I go out unless it's for a special occasion.
An alternative approach to this is that they cost a lot of money, so you're going to wear them to get the most out of them. I can't get myself to think this way. Can you?