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    Arts

    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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    Latest Episodes:
    Steven Klein on Breaking Rules, Beauty, and His Vogue Legacy Nov 28, 2025
    Show notes

    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.

    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.


    From Bloomingdale's Windows to Vogue's Inner Circle with Candy Pratts Price Nov 21, 2025
    Show notes

    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.

    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.


    Jawara Wauchope on Representation and Hair Artistry Nov 14, 2025
    Show notes

    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.

    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.


    Mickey Boardman: The Man Who Shaped Paper Magazine Nov 07, 2025
    Show notes

    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
    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.


    From Chicago's South Side to Fashion's Top: Law Roach's Story Oct 31, 2025
    Show notes

    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.

    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.


    Legendary Hair Artist Julien d'Ys Turns Hair into Art, History, and Poetry Oct 24, 2025
    Show notes

    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
    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.


    From Club Kid to Pop Culture Kingpin: Drew Elliot's Blueprint for Breaking the Internet Oct 17, 2025
    Show notes

    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.

    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.


    Gucci Westman: From Hollywood Makeup Artist to Beauty CEO - An Inside Look Oct 10, 2025
    Show notes

    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
    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.


    From Vogue's Legendary Closet to Styling Stardom: The Brian Coats Story Oct 03, 2025
    Show notes

    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.

    Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
    Follow on TikTok
    Send us your questions or comments by calling us at 518-21-ROGUE


    From Mrs. Astor to Anna Wintour: Billy Norwich's New York Sep 26, 2025
    Show notes

    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.

    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


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