Being a woman, I can say without embarrassment that I match the watch to the outfit for the day. On workdays I generally pick everything out the night before including watch and jewelry, wind up the watch and set it (day and date too, I am fussy), but I reserve the right to change my mind. I have certain more rugged watches that I will change out of when I finish doing whatever messy activity I was engaged in, and dress watches for evenings out, but otherwise I tend to wear the same one all day. In hot sticky weather I tend to rotate much less - there are a few that are most comfortable.
G