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Right Answers Mostly

Lilly Pulitzer and the Birth of Rich Girl Casual

37 min26 januari 2026

Before Lilly Pulitzer was splashed across sorority houses, bachelorette parties, and every preppy closet in America, she was just a Palm Beach socialite trying not to ruin her clothes while running a juice stand. What happened next accidentally created one of the most recognizable fashion empires of all time.


In this episode, Tess and Claire dive into how Lilly turned bright, stain-hiding shift dresses into a symbol of wealth, freedom, and rich girl rebellion and why her hot-pink prints quietly blew up the buttoned-up fashion rules of the 1950s and ’60s. We’re talking Jackie Kennedy (HINT HINT for future episode) in Palm Beach, old money social codes, glamorous breakdowns, scandalous divorces, and the rise of casual luxury before anyone was allowed to dress “effortless.”

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Created and produced by Tess Bellomo and Claire Donald


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Sources: Town and Country Magazine

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