My guest on today’s episode is podcast and radio producer Avery Trufelman. For about seven years, Avery was a producer for design and architecture podcast 99% Invisible, from which she eventually spun off her own podcast, Articles of Interest, which she describes as a podcast “about what we wear.”

I asked Avery on the show to talk about season 3 of the show, the entirety of which was dedicated to one topic, the story of preppy clothes and style in America. I was totally mesmerized by the seven episode season, which she titled “American Ivy.” It incorporates so many of the topics I’m interested in. Class, status, clothes, fashion, politics, Jews. It’s all in there in the story of prep, which runs through, among other focal points of cultural influence, elite universities, Jewish garment makers, Black civil rights activists and jazz musicians, Japanese obsessives, and every level of the extended Ralph Lauren preppy universe.

There's also a very personal angle we get into. Avery and I both went to prep schools. We both had complicated relationships with preppy style. She rebelled against it, pushing the dress code with Haight-Ashbury influenced vintage finds. I wanted to conform but never quite cracked the code. I knew the rules existed, but they were unwritten and opaque, the kind of thing you absorbed from family, from summer camps, from generations of insider knowledge. The right khakis, the right boat shoes, the right rollneck sweaters—not just the brand, but how they were worn, how they signaled status.It's a rich conversation. Hope you enjoy.

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