SHOW / EPISODE

The Official Preppy Handbook: The Original Influencer

Season 19 | Episode 283
1h 17m | Aug 24, 2026

Before Coastal Grandma and Grandmillenial, there was Preppy—and in the 1980s, it was practically a way of life. From Izods and penny loafers to monograms, madras, and The Official Preppy Handbook, we’re revisiting the look, the lore, and the aspirational fantasy that defined a certain corner of our Gen X childhoods.

In this episode, we share your hilarious and revealing listener comments and take a look at how the preppy aesthetic went from Ivy League campuses to suburban malls, television screens, and closets everywhere.

Carolyn shares how she deeply, unapologetically loved this book—and it informed far more of her life than she probably realized at the time.

But where did Kristin and Michelle fall on the Preppy Spectrum? Were they true preps, mall preps, reluctant preps—or no way in hell?

So grab your Izod, pop the collar and join us in our Volvo wagon for this trip down Memory Lane.

Find The Official Preppy Handbook here

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