How did Oxford shirts, cashmere sweaters, and chinos become staples of American fashion? How did a style born on Ivy League campuses make its way into the mainstream? What does the way we dress say about who we are?

To answer those questions, our producer, Caleb, sat down with Avery Trufelman, host of the podcast "American Ivy," and Maggie Bullock, author of the new book "The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew."