Tucking your pants leg into your boots?

I've read a few men's magazines that said a guy should never tuck his trousers unless there is a lot of snow and that's the only time it's acceptable. I've seen the same men's magazines showing thin guys with skinny leg jeans tucking their pants into there shoes/boots. I've also seen guys rolling up their pants to show off their boots or buying practically short-enough-to-be-capris jeans to flaunt their footwear. So what is proper way? I have a pair of these http://www.dtlr.com/product/shoes/levis-sahara-boot/black.html

and I can't show off much of the nice detail with the pants leg over them, but I don't want to look like I'm clueless or a try-hard. I usually wear dark to medium dark jeans and a black/dark grey/grey shirt (solid or graphic) with them along with a black peacoat.