I live where you get all four seasons - hot and humid summers and cold dark winters - so I tend to wear watches seasonally. In general, I wear smaller, slimmer, lighter watches in the depths of winter. When its real cold out, I'd rather not tuck a large or thick watch under tight sleeves, jacket cuffs, or gloves. Come summer, I tend to wear my larger and thicker watches. Spring and fall? Whatever I feel like, though it's usually dictated by whatever shirt or jacket I'm wearing on a given day.
At the end of the day, I want whatever watch I'm wearing to be comfortable and I have no problem not wearing a watch for a few months if it's not comfortable for how I'm dressing.