Going Rogue

Going Rogue

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?
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Episode's summary

When Zac Posen’s company closed in 2019, he spent weeks sitting by the fire. He grieved in a way he never had before and watched social media fill with what felt like public epitaphs for a life he wasn’t done living. He had lost his staff, his archive and the rights to his own name. For the first time since he was 22, he stayed in one place long enough to watch the seasons change. Jill's known Zac for more than 20 years, from borrowing dresses out of his atelier to helping get Christina Ricci out of a corset at the Met. In this conversation she asks him what all of it taught him. They talk about growing up in a SoHo loft with no bedroom walls and a painter father whose studio took up half the space, being held back a year with dyslexia, and dropping out of school at 19 because opportunity wouldn’t wait. Zac opens up about the people-pleasing that made him “too good a partner” to everyone but himself, and about going back to the mannequin in his father’s studio when he had nowhere else to work. That quiet…

Episodes

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From House of Z to Gap Inc.: Zac Posen Goes Rogue

When Zac Posen’s company closed in 2019, he spent weeks sitting by the fire. He grieved in a way he never had before and watched social media fill with what felt like public epitaphs for a life he wasn’t done living. He had lost his staff, his archive and the rights to his own name. For the first time since he was 22, he stayed in one place long enough to watch the seasons change. Jill's known Zac for more than 20 years, from borrowing dresses out of his atelier to helping get Christina Ricci out of a corset at the Met. In this conversation she asks him what all of it taught him. They talk about growing up in a SoHo loft with no bedroom walls and a painter father whose studio took up half the space, being held back a year with dyslexia, and dropping out of school at 19 because opportunity wouldn’t wait. Zac opens up about the people-pleasing that made him “too good a partner” to everyone but himself, and about going back to the mannequin in his father’s studio when he had nowhere else to work. That quiet…

30 Oct 2026
52-

Previously on Going Rogue: The Season 1 Recap

With season two launching next week, Jill borrows a page from television and looks back at some of her favorite moments from season one of Going Rogue. Writer Jonathan Van Meter, whose new book Citizen Kim is out October 27, recalls interviewing both Jennifer Aniston and Angelina Jolie. Hair stylist Orlando Pita shares the last-minute cancellation that launched his career, and Tonne Goodman remembers her unlikely start as a model. Photographer Steven Klein talks about honesty in images built on fiction, Phyllis Posnick tells some of her funniest Helmut Newton stories, and Nick Knight, founder of SHOWstudio, explains why artists need to embrace new technology. Mark Seliger revisits his first Nirvana cover for Rolling Stone and the small favor he asked of Kurt Cobain. Grace Coddington and Karen Mulligan reminisce about a Paris shoot with Ben Stiller and Annie Leibovitz, Norman Jean Roy explains why he has never needed a backup plan, and season one finale guest Priyanka Chopra Jonas talks about forgiving her…

23 Oct 2026
51-

Edward Enninful on Building EE72, Six Rihanna Covers, and Life After British Vogue

Jill sits down with Edward Enninful, the former British Vogue editor-in-chief who left the top of the masthead to build his own house. One year into EE72, the media and entertainment company he founded with his sister Akua, Enninful closes out 72 Magazine's first year with Rihanna on the cover, their sixth collaboration across W, British Vogue, and now 72. He and Jill trace their shared history from American Vogue in 2006 through the 40-icon British Vogue finale, then go deep on the new cover: the queen concept, photographer Szilveszter Makó's hand-painted backdrops, and why every Rihanna shoot happens overnight. Along the way: the '90s versus now, social media and the death of the curator, his Tate exhibition, advice for young creatives, and what he calls "the big flat," the collapse of silos between fashion, art, film, and music. Plus rogue rapid fire and a Prince versus Beyoncé question with only one possible answer. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky…

12 Jun 2026
50-

"Channel Your Best Andrea Sachs": Six Real Assistants of Vogue

With The Devil Wears Prada 2 hitting theaters this week, Jill pulls together moments from six former guests who actually lived the job, assisting Anna Wintour, André Leon Talley, Tonne Goodman, and Vogue's other most demanding desks. Leslie Fremar (yes, the real Emily), Brian Coats, Gabriella Karefa-Johnson, Edward Barsamian, Andrew Bevan, and Karla Martínez de Salas on the 18 trunks through customs, the faxes, the $10 lunch budgets, the run-throughs, and the sink-or-swim moments that built six remarkable careers. What Andrea Sachs couldn't handle in a day, these six did for years. 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…

01 May 2026
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The Devil Wears Prada: A Book, Two Movies, and Jill Demling

In a role reversal, Ned Martel takes the mic to interview Jill about her two decades at Vogue, timed to the release of The Devil Wears Prada 2. As the assistant who hired Lauren Weisberger, and the woman who turns up on page 21 of the novel, Jill has a firsthand stake in a story the culture keeps retelling. She walks Ned through the day the galley arrived, Anna's pivot from private hurt to public ownership of the movie, and her own running defense of the leather pants. From there the conversation opens into an oral history of the job. Jill describes Vogue in 1998: no iPhones, twenty-five handwritten phone messages waiting every morning, a diary read upside-down across the desk, and a telepathy with Anna so refined that hearing her own name was sometimes the whole question. She lays out the Monday fashion, Tuesday features, Thursday scheduling choreography, and the creative friction between Grace Coddington, Camilla Nickerson, and Anna that produced stories no other magazine could match. Jill and Ned trade…

24 Apr 2026