Trouser break for different types of shoes?

[Liquidus]

I need to get a pair of pants hemmed with a light break, and I plan to wear it both with chukka boots and leather oxfords. Should I have the tailor measure the appropriate length from the oxfords? If it was measured using the chukka boots, I think they would be too short when I wear oxfords. Thanks.

 

[pvrhye]

Think you outta have em cut for the lowest instep you wear. Just to be sure.