Her website, Man Repeller, offers witty and insightful ideas about fashion, not just as what we wear but as who we are: clothing as a window onto the larger culture. Although who’d want a window made of cotton? The rain would soak through, and you couldn’t see out. Metaphors: they only take you so far, but they take her to unexpected places in our conversation at JCC Manhattan. Plus music from Pete Rushefsky and Jake Shulman-Ment of the Center for Traditional Music and Dance.

•  PERSON: David Foster Wallace
•  PLACE: this porch, East Hampton
•  THING: this expensive ring
•  RANDY’S PERSON: Diana Vreeland