Jill sits down with celebrity stylist Leslie Fremar for a look at her remarkable career journey, from her early days as Anna Wintour's assistant to independent celebrity styling. Leslie takes us back to what it was really like being an assistant in fashion's golden era with the countless behind-the-scenes challenges that shaped her resilience. She opens up about her styling philosophy centered on timeless, quality pieces, and pays tribute to her most influential mentors, both Anna Wintour and Vogue editor Tonne Goodman, whose guidance helped shape her approach to fashion and career. Leslie shares stories from her transition to independent celebrity styling, including memorable moments working with Charlize Theron and styling for major red carpet events. She doesn't shy away from discussing the industry's tough realities, from grueling photo shoots to navigating customs with designer pieces, while offering hard-earned career wisdom for aspiring stylists about the value of apprenticeships and staying true to your authentic vision.

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

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.

Jill sits down with Versha Sharma, Editor-in-Chief of Teen Vogue, for the story of her climb to EIC at one of America's most influential youth publications. Sharma has taken the baton and is continuing Teen Vogue's mission to be more than a glossy guide to prom dresses by expanding it into a powerful platform for political discourse, social justice advocacy, and inclusive storytelling.

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

Jill talks with longtime Vogue colleague and renowned editor Tonne Goodman about her distinguished fashion career. 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.

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

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.

Jill sits down with her dear friend Karen Mulligan, the woman behind the legendary photographer Annie Leibovitz. Karen started as a production assistant at Annie's studio more than 25 years ago and worked her way up to become not only Annie's studio manager, but also her agent. Anyone who knows Karen knows she is Oz, making it all happen behind the curtain. It was on their first cover shoot together back in 2002 that Jill and Karen realized they had more in common than working long hours for two of the most influential women in the industry, and they have been best friends ever since.

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

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.

Jill chats with renowned hairstylist Orlando Pita to discuss his remarkable journey from self-taught Cuban immigrant to influential hair designer whose work has graced iconic Vogue covers and earned a place in the Smithsonian Design Triennial. Orlando opens up about his creative process and how his unconventional training freed him to innovate in hair styling, starting with cutting his family's hair and eventually working on high-profile shoots with Madonna, Beyoncé, and Lady Gaga.

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

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.

Renowned photographer Norman Jean Roy opens up about his unconventional journey to success, revealing how a winding path through architecture, and professional baking ultimately led him back to the camera.

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

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.

Jill welcomes legendary Vogue editor Phyllis Posnick for an intimate conversation about her extraordinary career that helped define fashion photography for decades. Karen Mulligan— agent and long-time studio manager for Annie Leibovitz—joins the discussion, offering insights into the collaborative process between editors and photographers. From her Long Island beginnings to becoming one of the most influential editors at Vogue, Posnick shares intimate stories about her collaborations with photography giants Irving Penn, Helmut Newton, Annie Leibovitz, and Steven Klein. Discover the behind-the-scenes magic of her most memorable shoots, the creative problem-solving that saved seemingly impossible situations, and her unique methodology for blending high fashion with compelling visual narratives. Posnick also reflects on the invaluable mentorship she received from Anna Wintour and Alexander Lieberman while offering aspiring creatives her hard-earned wisdom about patience, thorough preparation, and the collaborative spirit essential to creating iconic fashion imagery. This episode is an expert tutorial in visual storytelling from one of the industry's most respected visionaries.

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

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.

Jill chats with legendary journalist Jonathan Van Meter, whose byline has graced the pages of Vogue, Vanity Fair, and The New York Times. Jonathan pulls back the curtain on his extraordinary career interviewing Hollywood's elite—from emotional exchanges with Angelina Jolie to unforgettable moments with Jennifer Aniston and Lady Gaga.

From his humble beginnings studying theater to becoming the founding editor of Vibe magazine, Jonathan shares the pivotal moments that shaped his journalistic journey. Discover his secrets for creating the perfect interview environment, the challenges in profiling celebrities, and the decisions that led to his most powerful work.

This episode offers a masterclass in profile writing and a behind-the-scenes look at the vulnerable moments that never make it to print

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

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.

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? This podcast 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 creative people behind the scenes that made all the famous moments possible at Vogue

This isn't just a podcast about fashion. It's a podcast 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?

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

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.