Poor pics - in a rush
Warning: Spoiler! (Click to show)
I can't help but wonder how much more sophisticated this outfit would look if the watch was a thin dress watch with leather strap.
I am sure it's your favorite watch, but I see no difference between wearing a sports watch with a suit and replacing your dress shoes [or in this case, dress boots] with tennis shoes.
It is the same idea and creates the same image; one that is not harmonious.