In this special episode of Going Rogue, the tables are turned as Edward Barsamian steps in as host, putting Jill in the guest seat for an unscripted conversation. The two first met on a Vogue shoot with Blake Lively in 2009 and worked together for six years at the magazine. Less than a year into launching Going Rogue, Jill steps away from behind the microphone to share her own story, from her unconventional path into fashion to her nearly two decades shaping celebrity culture at American Vogue. Jill traces her journey from a math major at Colgate who wore Betsy Johnson catsuits to upstate New York bars, to a temp worker in LA who accidentally wandered into Rob Reiner's private bathroom, to landing a dream job as Anna Wintour's assistant without knowing who Anna Wintour was. She reveals the strategic thinking behind cover selection, the delicate dance of negotiating with publicists and studios, and how she helped transform British Vogue into a global competitor during her collaboration with Edward Enninful. Beyond the glamour and legendary shoots at places like Versailles, Jill opens up about what inspired her to create a podcast, why she ultimately left Vogue after 19 years, and what excites her about working with independent publications, including Edward Enninful's EE72 and Carine Roitfeld's CR Fashion Book. It's a rare chance to hear the woman behind the microphone tell her own story.

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Jill sits down with stylist Natasha Royt, who cut her teeth under two of fashion's most formidable editors, Phyllis Posnick and Camilla Nickerson. Natasha takes us inside her years at Vogue, where she worked alongside photographers Irving Penn and Helmut Newton, and opens up about the long process of stepping out from under those towering influences to develop a creative identity of her own. She talks about the tension between precision and instinct in image-making, the holistic philosophy she brings to both her work and her life, and what she's seeing in fashion's shifting landscape. Plus, Natasha introduces her new Substack, First Option, a newsletter bringing together sharp shopping advice, styling know-how, and lifestyle inspiration, all filtered through her dual life as a veteran fashion stylist, devoted yogi, and spiritual seeker.

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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.

Karen Elson shares her remarkable journey from an unconventional supermodel to a musician, activist, and aspiring actor. Known for her signature pale skin, red hair, and unique beauty, Karen made waves in the fashion industry by gracing over 30 international Vogue covers and walking the runways for major designers like McQueen, Chanel, and Versace. She discusses her early struggles with bullying and an eating disorder, finding solace and inspiration in fashion magazines. Jill delves into Karen’s transformative experiences with iconic photographers like Steven Meisel, Tim Walker, and Peter Lindbergh, highlighting her collaborative spirit and willingness to push boundaries. Karen also touches on her activism work, including fighting for models' rights and her insights into the shifts within the fashion industry.

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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.

Jill sits down with visionary creative director Nicola Formichetti for an conversation about his journey through the fashion world. Known for his work with Lady Gaga, his tenure at Diesel, and his current role at MAC Cosmetics, Nicola opens up about the experiences that shaped his approach to fashion and creativity. Nicola takes us back to his early days exploring the flea markets of Rome and traces his path to working at the highest levels of global fashion. He gets real about his boundary-pushing approach to creativity and why embracing mistakes has been key to his success. Nicola sharing what it was really like creating some of fashion's most memorable imagery with photographers like Nick Knight and Steven Klein. Nicola also talks about his current role at MAC Cosmetics, where he's bringing his vision to beauty and fashion. He's all breaking rules, challenging the status quo, and trusting your creative instincts, even when you're not sure where you're headed.

Along the way, Nicola mentions the people who've shaped his path, including his mother, Alister Mackie, Katie Grand, Katy England, Jefferson Hack, Kim Jones, Gwen Stefani, Richard Burbridge, Miles Aldridge, Anna Cockburn, Tomo Koizumi, Eugene Tong, and James Gager.

For anyone interested in innovation, creative courage, and authentic self-expression in fashion and beyond, this conversation offers plenty to think about.

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Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer

Jill chats with Stefan Beckman, one of fashion's most influential set designers. Over 25 years, Beckman has created unforgettable environments for Marc Jacobs, Chanel, Prada, and Louis Vuitton while collaborating with photography icons Steven Meisel, Peter Lindbergh, Steven Klein, Tim Walker, Craig McDean, Herb Ritts, and Fabian Baron. Stefan traces his path from theater and film school to becoming fashion's go-to set designer, revealing the creative process behind landmark fashion shows and editorial shoots. He discusses how his formative years shaped his visual approach and shares his perspective on where set design is headed as the industry transforms. Stefan recounts memorable moments with Whitney Houston, Notorious B.I.G., Cher, JLo, the Rolling Stones, LL Cool J, Jamie Foxx, Gwyneth Paltrow, Winona Ryder, Gisele Bündchen, Renee Zellweger, Amber Valletta, Matt Damon, Jake Gyllenhaal, Daria Werbowy, Kate Hudson, Owen Wilson, Rihanna, Billie Eilish, Angelina Jolie, and Beyoncé. Check out the video on our YouTube channel with many of the images discussed in this episode

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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.

Jill sits down with writer and editor, Ned Martel, who shares his experiences working with two of the most daring magazine experiments of our time, George Magazine with John F. Kennedy Jr., and Men's Vogue under Jay Fielden. What made these publications revolutionary, the cultural and creative challenges they faced, and the eventual shuttering of both titles. Martel also opens up about the personal impacts of losing close friends and navigating the media landscape as a gay man. Martel offers insights into the history of magazines, journalism, and ambitious storytelling.

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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.

For over four decades, Paul Cavaco has been fashion's invisible hand, the editor who shapes the iconic images we see but rarely thinks about who made them possible. In this episode, Jill sits down with Paul to talk about his work at Harper's Bazaar, Vogue, and Allure, and what it takes to create images that actually mean something. He shares stories about collaborating with photographers like Richard Avedon, Steven Meisel, Annie Leibovitz, and Bruce Weber, and explains the chemistry between editors and photographers that turns a photo shoot into something memorable. Paul also talks about the difference between style and trends, his path from the Bronx to the center of American fashion, and how the industry has changed over the years.

If you're into these conversations, rate, review, and subscribe to keep them going!

Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
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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.

Note: This re-released episode from June 2025 features Tonne Goodman, longtime fashion director at American Vogue who styled over 200 covers, most with Jill. Tonne witnessed fashion's seismic shift from photographer-first covers to celebrity-driven ones, working under Liz Tilberis at Harper's Bazaar and Anna Wintour at Vogue. This episode returns now because next week's guest, Paul Cavaco, shares a deeply intertwined career with Tonne. They were co-fashion directors at Bazaar before Tonne took over when Paul left for Allure. Like her signature uniform of white jeans, loafers, and a silk scarf, Tonne's work has always been about clarity over noise.

Tonne shares her path from art school and early modeling to working with Calvin Klein before joining American Vogue, where she was mentored by the legendary Diana Vreeland. She recounts behind-the-scenes stories from high-profile celebrity shoots featuring stars like Angelina Jolie, Charlize Theron, and Britney Spears, and discusses her collaborations with top photographers including Mario Testino, Steven Meisel, Herb Ritts, and Annie Leibovitz. As they explore her career, Tonne emphasizes the collaborative spirit essential to successful fashion shoots and her diplomatic approach to managing complex productions. Drawing from her own experience as a former model, she reveals her fierce commitment to advocating for and protecting the talent she works with.

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Send us your questions or comments by calling us at 518-21-ROGUE