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Going Rogue
Going Rogue
Author: Radio Free Rhinecliff
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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?
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?
43 Episodes
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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
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.
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.
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.
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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Jill chats with Francelle Daly, a renowned New Orleans-born makeup artist whose journey to the top was fueled by pure hustle and determination. Beginning her career at the Saks makeup counter, Francelle quickly scaled the ranks, working on sets with legendary photographers like Annie Leibovitz and Craig McDean. Francelle shares the story of her unconventional path, her resilience in the face of industry challenges, and her experiences working on high-stakes projects like a celebrity cruise campaign during the pandemic. Francelle also delves into her collaboration with iconic figures such as Grace Coddington and Phyllis Posnick, and the creative freedom she experiences working with independent magazines. She talks about the inception and philosophy behind her brand, Lovecraft Beauty, a venture that aims to build a creative community. Francelle shares lessons on perseverance, innovation, and the power of following one's passion.
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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.
Join Jill for a conversation with iconic image maker Nick Knight. For over 40 years, Knight has redefined fashion imagery, working with i-D, Vogue, and W. From documenting street culture and collaborating with Yohji Yamamoto, Linda Evangelista, and British Vogue to founding SHOWstudio and creating projects with Alexander McQueen, Björk, Lady Gaga, and Kanye West, Knight has transformed how fashion is seen and experienced. He discusses his philosophy that photography is about creating what you want to see rather than capturing reality, addressing digital photography, AI, and the importance of moving forward. Reflections on past collaborations and thoughts on the future of fashion and technology.
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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 talks with Garren, the legendary hairstylist who shaped fashion history over five decades. From his modest beginnings in a basement salon in Niagara Falls to becoming a fixture at Bergdorf Goodman and a trusted creative partner to photographers like Irving Penn, Richard Avedon, and Steven Meisel, Garren's journey is nothing short of extraordinary. They explore his work on transformative looks: Farrah Fawcett's feathered waves, Linda Evangelista's endless reinventions, and signature styles for Victoria Beckham and Karlie Kloss. Garren reflects on his collaborative relationships with fashion greats including Patrick Demarchelier, Bill King, and Arthur Elgort, plus challenging editorial shoots with Polly Mellen, Phyllis Posnick, Grace Coddington, and Tonne Goodman. From the evolution of hairstyling and the importance of mentorship to the industry's shift in the Instagram and AI era, it's a master class in fashion history for anyone who loves the craft.
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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 is a re-released episode from June 2025. When Jill sat down with Versha Sharma, she was Editor-in-Chief of Teen Vogue. Since then, Condé Nast has folded Teen Vogue into vogue.com, eliminating the masthead entirely. Sharma's job and the editorial identity she built were swept away in that restructuring, which is exactly why this conversation feels even more relevant now.
Jill sits down with Versha Sharma for the story of her climb to EIC at one of America's most influential youth publications. Drawing from her Louisiana upbringing as the daughter of Indian immigrants, Sharma opens up about the feelings of otherness that fueled her passion for amplifying marginalized voices. The conversation traces her path from Obama's 2008 campaign through her evolution into journalism and her leadership at Teen Vogue during COVID-19 and the social justice reckoning of 2020.
Sharma describes the strategic evolution she guided, from embracing digital-first publishing to prioritizing video content for Gen Z audiences. The episode highlights groundbreaking editorial choices under her guidance, including features on Vivian Wilson, Elon Musk's transgender daughter, and Representative Maxwell Frost, the first Gen Z member of Congress.
Listening back, this conversation is a reminder of what leadership actually looks like in media and how much is lost when the industry sidelines the voices who push it forward.
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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
Jill speaks with iconic artist and photographer Steven Klein for an intimate exploration of his groundbreaking career. Renowned for his transgressive, culturally resonant imagery, Klein discusses his new book 'Steven Klein Vogue,' which chronicles two decades of boundary-pushing work within mainstream fashion photography. The conversation traces his journey from his Rhode Island upbringing through his transformative collaborations with Anna Wintour, Grace Coddington, Phyllis Posnick, Garren, Kate Betts, and Liz Tilberis at Vogue. Klein reflects on working with legendary figures including Alexander McQueen, Madonna, Prince, Pat McGrath, Angelina Jolie, Nicole Kidman, Beyoncé, Rihanna, Gisele Bündchen, Brad Pitt, and countless other luminaries who have shaped contemporary fashion and culture.
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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 chats with legendary fashion insider Candy Pratts Price, whose decades-long career has left an indelible mark on the industry. From revolutionizing Bloomingdale's windows to pioneering digital fashion journalism at style.com to serving as Anna Wintour's right hand at Vogue, Candy has been a transformative force behind fashion's biggest cultural moments. She shares her journey from Washington Heights to the industry's highest echelons, offering her unique philosophy on fashion as entertainment and reflecting on how the cultural landscape has evolved throughout her career. Through personal anecdotes and hard-won insights, Candy reveals what it takes to modernize an industry while remaining one of its most powerful yet unseen influencers. For visuals discussed in the episode, visit the Going Rogue podcast's Instagram.
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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 talks with Jawara Wauchope about his journey, whose passion for hairstyling began at age six, sweeping floors in a Kingston salon and eventually transforming his sister into a music video muse. Born in Brooklyn and raised in Jamaica until he was ten, Jawara returned to Queens and pursued an unconventional path through salon apprenticeships and the Fashion Institute of Technology (FIT). After years assisting fashion legends like Guido Palau, Sam McKnight, Luigi Murenu, and Paul Hanlon, he mastered techniques for working with any hair type at the highest level. His breakthrough came in 2013 when he went solo. From Vogue covers to Beyoncé's Renaissance shoot for British Vogue and Rihanna's first pregnancy reveal for American Vogue, Jawara hasn't just broken barriers: he's championed representation and elevated Black hair artistry to the forefront of fashion.
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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 chats with Mickey Boardman, also known as Mr. Mickey, the cultural tastemaker and heart of Paper Magazine for the past three decades. From his beginnings as a kid in suburban Illinois obsessed with glamor to becoming New York's most beloved cultural tastemaker, Mickey shares his journey, including insights into the famous Kim Kardashian 'Break the Internet' cover, his unique editorial vision, and his passion for celebrating creativity and authenticity. Through stories of his early work, internships, and transformative moments at Paper, Mickey reveals how he embraced his uniqueness and helped shape the magazine industry.
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.
Jill welcomes Law Roach, the visionary stylist who transformed Zendaya into a fashion icon. As the first Black stylist to top the Hollywood Reporter's power list and win the CFDA's Inaugural Stylist Award, Law traces his evolution from Chicago's South Side to founding Deliciously Vintage to becoming one of fashion's most influential voices. He reveals the psychology driving his distinctive styling approach, explains his revolutionary concept of method dressing, and shares the personal mantras that fuel his work. Discover how his partnership with Zendaya began, the strategies he used to overcome industry gatekeeping, and why he believes magazines remain essential to a stylist's success. Law's philosophy on confidence and his rule-breaking approach to fashion offer a masterclass in reshaping an industry. Jill’s conversation captures the vision and legacy of a stylist who fundamentally changed the game.
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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 welcomes a pioneering hair artist whose work has shaped the industry for almost forty years. Julien d'Ys has graced the pages of Vogue, styled iconic supermodels, and showcased his artistry at the Met Costume Institute in New York. Celebrated for transcending conventional boundaries, Julien has elevated hair into an art form that fuses fantasy, historical references, and sculptural vision. Julien reflects on his creative path, his partnerships with legendary photographers including Steven Meisel, Irving Penn, and Peter Lindbergh, and the artistic influences spanning surrealism, history, and pure imagination that fuel his work. He discusses his approach to beauty and creativity, the formative experiences that shaped his career, and his unforgettable contributions to fashion's most iconic moments.
Click HERE for a searchable who's who on this episode
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.
Jill chats with Drew Elliot, the visionary cultural architect who transformed entertainment media from the inside out. From his roots as an entertainment-obsessed kid in Indiana to becoming the creative force who popularized "Break the Internet" and turned it into a cultural phenomenon, Drew's journey is a masterclass in cultural disruption.
Explore Drew's groundbreaking tenure at Paper Magazine, where he orchestrated iconic moments with A-list celebrities that helped define digital culture. He shares the philosophy behind his success: surrounding himself with geniuses, demolishing creative boundaries, and cultivating an inclusive environment where the next generation of talent can thrive. Drew shares his insights into innovation, creativity, and what it really takes to shape culture in the digital age.
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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 chats with renowned makeup artist and CEO Gucci Westman. Gucci shares her journey from her unique upbringing on a California ashram to becoming one of Hollywood's most sought-after makeup artists, working with directors like David Lynch and Michael Bay. They discuss her breakthrough into high-fashion covers and editorial spreads, a pivotal move propelled by Grace Coddington, and her successful leap into entrepreneurship with the launch of her clean luxury beauty brand, Westman Atelier. Join them as they reminisce about memorable celebrity shoots, the evolution of the fashion and beauty industry, and Gucci's passion for creating high-performance, skincare-infused makeup.
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.
Jill welcomes the always charming Brian Coats, affectionately known as "the boy in the closet," for an intimate conversation about his remarkable journey through fashion's most prestigious corridors.
Brian's fashion odyssey began in 1996 as an assistant at Vogue Magazine, where he commanded the legendary fashion closet and collaborated with the incomparable Andre Leon Talley. Together, they unpack colorful behind-the-scenes tales from those formative years, from the infamous closet smoking incident to the daily choreography of managing fashion's most coveted archive, a central hub of activity and competition for the editorial and styling teams.
The story reaches back even further, to six-year-old Brian in North Carolina, mesmerized by Elsa Klensch's CNN style segments, a moment that ignited a lifelong passion. He recounts his unwavering determination to reach Parsons School of Design and the pivotal realization that his destiny lay in editorial styling rather than design.
In 2000, Brian transitioned to GQ, where he honed his craft as a fashion editor for 13 years before embracing the freelance world. He candidly discusses the adjustment, from overpreparing for his first independent shoot to navigating an industry landscape without a magazine masthead behind his name.
The conversation turns to Brian's current work styling high-profile magazine spreads, advertising campaigns, and celebrities, including his continued partnership with Jimmy Fallon. Jill and Brian examine the contrasts between Vogue and GQ cultures, the art of juggling competing demands and personalities, and surviving fashion's relentless pace.
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Step into the world of Billy Norwich in this second part of an intimate and expansive conversation with Jill. Billy reflects on his career spanning decades, including his work as a gossip columnist for the New York Daily News and the New York Post, and his editorial roles at Vogue and other prestigious publications. As someone uniquely positioned at the intersection of old New York and new New York society, Billy shares fascinating encounters with figures ranging from Mrs. Astor to Malcolm Forbes, offering a rare perspective on the evolution of high society. Hear about his personal anecdotes involving colorful characters like Donald Trump, Kim Kardashian, and John F. Kennedy Jr., and get a glimpse into the changing landscape of journalism and fashion. Billy shares heartfelt stories, including his experiences with significant figures like Liz Smith and Evelyn Lauder, and opens up about his deep, enduring friendship with Anna Wintour that has shaped both his personal and professional life. He discusses his novels 'Learning to Drive' and 'My Mrs. Brown,' navigating relationships, the impact of life events on his work, and finding meaning in the objects and memories that surround him. This part continues a thoughtful exploration of legacy, memory, and storytelling, offering unique insights from a man who has witnessed the transformation of New York's social fabric and continues to find joy and purpose in his journey.
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