RD 2006 March issueの次のジョークにビジネス英語、教科書英語ではまずお目にかからない「(靴を)履き慣らす」にあたると思われる表現がありました。
While sitting in New York’s Central Park, I watched a little girl as she dragged herself up a path behind her mother.
“Mummy,” she griped loudly, “my feet are so tired.”
“Well, of course you feet are tired,” said the intrepid mother, still charging ahead.
“They’re only five years old. You’ve got to break them in.”
最後の "break them in" は、靴を履き慣らすの意味でしょう。