I should think rain would be an immediate argument in favor of boots. Next would be fashion, unless you are a woodsman or work an oil rig.
Personally I have a hard time incorporating boots without invoking the generic, Made-in-USA, Americana look that I feel has run it's course over here. That being said, I could still go for a pair of Alden Indies or plain toe boots.
I just picked up some Chelseas made by Cheaney, in order to give the whole Hedi Slimane thing a go (not really - my jeans don't have holes).
I recognize that you are likely asking the question in regards to a more polished, formal look. I wear my shirts untucked, so cannot much speak to that, other than dress boots do go well with tweed and heavy wools in general.
Edited by whorishconsumer - 10/18/16 at 1:01pm