Going Rogue

Grace Coddington doesn't just style pictures, she builds worlds. In this rare and unfiltered conversation, the legendary creative director sits down with Jill and longtime friend Karen Mulligan to talk about the images that defined her and the ones that almost broke her.

From her early modeling days and Beatrix Miller's British Vogue to the Anna Wintour era in New York, Grace reflects on a career shaped by instinct, irreverence,...

Jill visits with Mark Healy, an experienced editor and writer recognized for his sharp insights into media influence and power dynamics. Together, Jill and Mark reminisce about their days at Condé Nast during what many regard as the company's golden age. They reflect on Condé Nast's unmistakable company ethos, from its unwritten codes of conduct like elevator silence to the subtle markers of hierarchy and achievement. They also tra...

Jill is joined by Mary Howard, a renowned set and production designer celebrated for crafting captivating, detailed environments for top fashion photographers. Mary traces her unconventional path from junior tennis player and art student in New Orleans to working alongside industry legends like Annie Leibovitz, Steven Meisel, and Steven Klein. She reveals her creative methodology for bringing conceptual visions to life in three dim...

Adam Green joins Jill to explore his evolution from screenwriter to Vogue's acclaimed theater critic. As the son of Broadway royalty Phyllis Newman and Adolf Green, he brings unique perspective to profiling entertainment's biggest names. Green shares intimate glimpses from his celebrity interviews, including a cringe-worthy childhood memory involving Bernadette Peters, the surreal experience of questioning Cate Blanchett during an ...

Jill chats with fashion stylist Gabriella Karefa-Johnson, a fashion force who’s made it her mission to shake up the industry from the inside out. Gabriella shares her journey at Vogue from working as associate fashion editor for fashion director Tonne Goodman to becoming the first Black woman to style a Vogue cover in January of 2021 with her styling of model Paloma Elsesser. Her distinctive approach, which is layered, joyful, and ...

Jill sits down with renowned makeup artist Stéphane Marais for an in-depth conversation about his cinematic approach to beauty. Over his thirty-year career, Stéphane has evolved from admiring Marlene Dietrich's elegance to creating iconic looks for stars like Rihanna.
Stéphane describes his signature style as centering on character creation. His trademark smudged black eyeliner technique transforms eyes into captivating focal p...

Jill catches up with Andrew Bevan, her former assistant at Vogue who's proven that being different is the quality that would define his career. The kid from Colorado who won best dressed in high school with a style he describes as "Gene Kelly meets Winona Ryder" has always been ahead of the trend, confident in his aesthetic even when others couldn't understand it. From aspiring Broadway star to Teen Vogue Style Director, Andrew ope...

Before the covers, there was the interview. In this special bonus episode of Going Rogue, Jill guides us through an oral history. Grace Coddington, Phyllis Posnick, Norman Jean Roy, and other Vogue insiders take us back to their first encounter with Anna Wintour. They might not remember what they said. But ask them what they wore? Every single detail. The Olivier Theyskens skirt they couldn't afford, the Target top that had to pass...

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 ...

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.
Drawing from her Louisiana upbringing as t...

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,...

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...

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-p...

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. Norman shares his perspective on overcoming the fear of failure, drawing from decades of photographing celebrities and models for Vogue and other publications. He explores the emotional depth required for powerful portrait photog...

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, Po...

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, Jon...

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?...