I don't own, or plan to have, anything special or very expensive.
On my day-to-day activities the one that I wear most is the Speedmaster:
This one is the sapphire sandwich version. Not fancy but somehow reliable.
Normally I rotate this one with another Speedmaster, also Moon but vintage.
My few others, I wear during very special occasions or weekends.
After one gets robbed, like I was last year, this changes our view of watches.
Cheers