Show Notes
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
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.
More from Going Rogue
With season two launching next week, Jill borrows a page from television and looks back at some of her favorite moments from season one of Going Rogue.
Jill sits down with Edward Enninful, the former British Vogue editor-in-chief who left the top of the masthead to build his own house. One year into EE72, the media and entertainment company he founded with his sister Akua, Enninful closes out 72 Magazine's first year with Rihanna on the cover, their sixth collaboration across W, British Vogue, and now 72. He and Jill trace their shared history from American Vogue in 2006 through the 40-icon British Vogue finale, then go deep on the new cover: the queen concept, photographer Szilveszter Makó's hand-painted backdrops, and why every Rihanna shoot happens overnight. Along the way: the '90s versus now, social media and the death of the curator, his Tate exhibition, advice for young creatives, and what he calls "the big flat," the collapse of silos between fashion, art, film, and music. Plus rogue rapid fire and a Prince versus Beyoncé question with only one possible answer.
With The Devil Wears Prada 2 hitting theaters this week, Jill pulls together moments from six former guests who actually lived the job, assisting Anna Wintour, André Leon Talley, Tonne Goodman, and Vogue's other most demanding desks. Leslie Fremar (yes, the real Emily), Brian Coats, Gabriella Karefa-Johnson, Edward Barsamian, Andrew Bevan, and Karla Martínez de Salas on the 18 trunks through customs, the faxes, the $10 lunch budgets, the run-throughs, and the sink-or-swim moments that built six remarkable careers. What Andrea Sachs couldn't handle in a day, these six did for years.
In a role reversal, Ned Martel takes the mic to interview Jill about her two decades at Vogue, timed to the release of The Devil Wears Prada 2. As the assistant who hired Lauren Weisberger, and the woman who turns up on page 21 of the novel, Jill has a firsthand stake in a story the culture keeps retelling. She walks Ned through the day the galley arrived, Anna's pivot from private hurt to public ownership of the movie, and her own running defense of the leather pants.