Calvin Klein: Underwear, Supermodels, and Scandal

From Right Answers Mostly by Claire Donald & Tess Bellomo

May 11, 2026 · 54 min

About this episode

This episode explores the transformative impact of Calvin Klein on the fashion industry and culture.

Before Calvin Klein, underwear was something your mom bought in a three pack. After him? It was a personality. This week, we’re getting into the story of Calvin Klein, how a kid from the Bronx turned “clean and simple” into one of the most powerful fashion brands in the world. We’re talking jeans that made millions in a week, ads that changed culture, and the women who defined the look (and the vibe). Plus: the Kelly Rector influence, Carolyn Bessette Kennedy’s quiet takeover of the aesthetic, and the business missteps that almost took the whole empire down. Created and produced by Tess Bellomo & Claire Donald For more RAM and to learn about us, go here! If you are interested in THREE bonus episodes a month (pop culture, our own personal lives, and the full history episode at the end of the month) go here! only $7.99/month or save 13% when you buy annually! Thanks to Bellesa for sponsoring today's episode!EVERYONE who signs up wins a FREE WhisperVibe™ OR a FREE Rose toy with any Whisper™ order! https://www.bboutique.co/vibe/rightanswersmostly-podcast Learn more about your ad choices. Visit podcastchoices.com/adchoices

People in this episode

Hosts: Claire Donald, Tess Bellomo

Topics covered

fashion history
Calvin Klein
supermodels
advertising
cultural impact

Keywords

Calvin Klein
underwear
supermodels
fashion brand
advertising

Mentioned in this episode

Organizations: Right Answers Mostly

Places: Bronx