Ask your tailor to end the hem of your pants no more than ½ of the way down the shoe. Your socks will show slightly when you are standing and walking so make sure you are wearing your favorite pair.
To achieve a full break, the length of the trousers should reach well beyond the ankles to at least midway down the counter of the shoe, and the opening width should be wide enough for the leg opening to fit around the laces.
Your jeans should just meet the top of your boots; an effortless look that says you're ready for anything.