Going Rogue

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

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

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

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

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

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

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