My current 3-watch rotation. For me it's not about the occasion so much as my mood. There are other watches I like, but in general I have what I want. That's the Holy Trinity for me. I could substitute in a Patek Aquanaut or an SD4K, but they wouldn't get as much wear as the three in the pics.
All of my watches are everyday watches since they are all in my daily rotation so I have slightly different categories: casual dress, chronograph, GADA tool watch. I still have to purchase the Explorer but I am going back and forth between a 36mm and the 39mm.