I thought about this for a while myself. Honestly, I'm my happy self when I'm wearing casual clothes and a sportier, perhaps bulkier watch.
I know there are technical rules about what size watch is "correct" and what would be appropriate in a formal or dressy occasion. Since I could only afford one watch, I was hesitant to get one watch that would "break the rules" in certain occasions.
But then I realized I should prioritize getting a watch that I am happy with most of the time, instead of focusing on what "works" in very limited situations (where I'm probably not happy with the rest of my clothes anyway). I've made my peace that I will annoy some people in some situations for breaking the rules.
I know there are technical rules about what size watch is "correct" and what would be appropriate in a formal or dressy occasion. Since I could only afford one watch, I was hesitant to get one watch that would "break the rules" in certain occasions.
But then I realized I should prioritize getting a watch that I am happy with most of the time, instead of focusing on what "works" in very limited situations (where I'm probably not happy with the rest of my clothes anyway). I've made my peace that I will annoy some people in some situations for breaking the rules.