Going Rogue

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 a...

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 co...

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...

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...

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.

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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...

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...

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...

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. <...

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...

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...

Jill sits down with the incomparable Billy Norwich for an intimate conversation about his remarkable 40-year reign chronicling New York society, from dishing gossip at the Daily News and Post to his glamorous two decades shaping stories at Vogue. Billy spills on his storytelling philosophy, shaped by Anna Wintour's advice to "edit your life" and his personal theory of the "anthropology of style."

The conversation takes a very personal turn as Billy opens up about losing his father at nine and mother by nineteen. These heartbreaking losses could have destroyed him but instead deepened his determination. He...

Jill sits down with renowned makeup artist Dick Page, whose rebellious approach to beauty has left an indelible mark on fashion's visual landscape. Known for his mantra that "makeup should be fun, not a chore," Dick shares his unconventional philosophy that sees makeup as a creative canvas rather than a corrective tool. Dick opens up about his unexpected beginnings—from fascination with the varying shades of red he observed working in a slaughterhouse as a teenager, to his journey through London's photo processing labs in the early '90s before landing in New York. Without formal training but armed wi...

Jill sits down with her friend and colleague Edward Barsamian to explore his fascinating decade-long journey through fashion media. Edward shares stories from his impressive career path, starting as a style director at Vogue where he closely followed airport looks and red carpet appearances of stars like Amal Clooney and Zoe Kravitz, then moving into the digital world of celebrity fashion coverage.
The conversation covers Edward's early Vogue years, his time at Gilt Group and The New York Times Style Magazine, and his return to Vogue in a major digital position. Edward recounts his experiences at glamorous events...

Jill sits with Christiaan, the legendary hairstylist who has shaped the beauty industry for over five decades. Known for creating iconic looks including Debbie Harry's signature shag and Grace Jones' striking flat top, Christiaan is also credited with inventing the revolutionary undercut years before it became mainstream. His distinguished career includes collaborations with renowned photographers Arthur Elgort, Peter Lindbergh, Richard Avedon, Irving Penn, and Mario Testino, while styling supermodels Naomi Campbell, Christy Turlington, and Linda Evangelista for leading publications like Vogue and Harper's Bazaar.
Christiaan's remarkable journey began in a small Dutch village, working in his father's barbershop...

Jill sits down with legendary photographer Mark Seliger to hear how he went from small-town Amarillo, Texas, to defining rock and roll imagery for an entire generation. As Rolling Stone's chief photographer for a decade, Mark shot an incredible 188 covers and opens up about his tricks for catching those real, unguarded moments that make his photos so striking. He talks about making the leap to New York City in 1984, the photographer friends who helped him along the way, and landing those career-defining Rolling Stone gigs. You'll hear about his iconic shots including Kurt Cobain's final portraits and Jerry Seinfeld's...

Jill welcomes Karla Martínez de Salas, the Editor-in-Chief of Vogue Mexico and Vogue Latin America. Karla’s illustrious fashion journey began at Vogue as a fashion assistant at American Vogue in 2002. Today, she holds a prominent position at the helm of Vogue's Latin American editions. Karla shares her experiences growing up in a bicultural environment in El Paso, Texas, and how her fascination with fashion and journalism started at a young age. She discusses the differences between Vogue Mexico and Vogue Latin America, including the logistical and cultural variations they navigate each month. Karla also reflects on her tim...

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, and one very iconic hairdo. She revisits the chaos of the Wizard of Oz shoot with Keira Knightley, the comic genius of Ben Stiller's Funny Face spoof...

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 trace Mark's career trajectory beginning with his early role at Playboy through his transformative work at Details and GQ, where he helped reshape both magazines' identities. Mark shares how Details positioned it...

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 dimensions, emphasizing how every small element matters in her designs. Mary reflects on formative experiences building elaborate Mardi Gras floats and working on the Macy's Thanksgiving Parade, which developed her production expertise. She recounts standout Vogue...

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 eccentric theatrical production, and the complexities of a challenging sit-down with Vanessa Redgrave. The conversation takes a playful turn as Jill prompts Adam to evaluate how Hollywood stars like Amanda Peet, Jake Gyllenhaal, and Sienna Miller fared in their...

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 purposeful, emphasizes support for emerging designers and size inclusivity, though her outspoken advocacy has led to industry conflicts. They delve into Gabriella's roots in Ojai, California, her grandparents' fo...

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 points, while his preference for finger application creates an organic, personal touch.
He traces his creative roots to childhood influences spanning classic cinema and the landscapes of Africa and France. This early exposure drew him...

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 opens up about his unconventional path through the fashion world, sharing incredible behind-the-scenes stories including booking cowboys, matadors and monks, oh my! Andrew unpacks his shift...

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 for designer, the Manolos borrowed from the closet...
When you're about to meet Anna, you don't just prepare your answers. You prepare your look. As...

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...

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 the daughter of Indian immigrants, Sharma opens up about dealing with feelings of otherness and isolation that ultimately fueled her passion for amplifying marginalized voices in the magazine. The...

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...

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...

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.
They explore his pioneering approach to hair as visual art and examine the dynamics of collaborating with photographers and editors while navigating the shift from w...

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 photography and discusses how revisiting his own work with maturity has deepened his understanding of the human condition.
Norman also shares how a life-changing accident reignited his passion and pulled him back to photography. His story...

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 meth...

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 wo...

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...