Everyone Remembers Their First Time... with Anna

Before the covers, there was the interview. In this special bonus episode of Going Rogue, Jill guides us through an oral history. Grace Coddington, Phyllis Posnick, Norman Jean Roy, and other Vogue insiders take us back to their first encounter with Anna Wintour. They might not remember what they said. But ask them what they wore? Every single detail. The Olivier Theyskens skirt they couldn't afford, the Target top that had to pass for designer, the Manolos borrowed from the closet... When you're about to meet Anna, you don't just prepare your answers. You prepare your look. As Anna turns the page, they remember how their stories began—with that first interview. Everyone remembers their first time… with Anna. Featuring: Grace Coddington, Phyllis Posnick, Norman Jean Roy, Tonne Goodman, Karla Martinez de Salas, Gabby Karefa-Johnson, Versha Sharma, Leslie Fremar, Edward Barsamian, Brian Coats, Andrew Bevan, and Jill Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.

Om Podcasten

Welcome to the ultimate insider's guide to the world of fashion, celebrity, and media—straight from the heart of Vogue. I’m Jill Demling and for nearly two decades I was the Entertainment Director of Vogue. I've booked over 200 American Vogue covers, 30 covers for British Vogue, and more than 50 covers worldwide. That's nearly 300 covers that shaped pop culture, defined fashion, and captured the zeitgeist. But those perfect images? They're just the tip of the iceberg. "Going Rogue" is your backstage pass to the moments that never made it to print. The stories from the photographers who captured magic, the stylists who created iconic looks, and the writers who know every secret. You'll hear about the celebrities, the shoots that almost didn't happen, and the untold drama behind fashion's most memorable moments. Remember "The Devil Wears Prada"? That fictional 11-month snapshot? I was there for the real story—I even hired the person the book was based on and appear on page 21 of the book. But this isn't about one story. It's about hundreds of stories, from someone who was on the inside. This podcast is not an exposé, it's a celebration of the brilliant people behind the scenes that made all the famous moments possible at Vogue. It isn't just a podcast about fashion. It's about creativity, ambition, art, and the human stories behind the images that helped define a generation. We'll reveal how the talents behind these shoots got their start, and they'll share masterclass-level advice for a new generation of stylists, photographers, and creatives looking to make their mark. We're going behind the scenes of a world most people only glimpse through glossy pages and red carpet moments. Are you ready to go rogue with me?