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Trouser break for different types of shoes?

Liquidus

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Joined
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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.
 

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