I Did A Masterclass With Anna Wintour – And This Is What Happened

With one of the fashion industry’s most recognisable names, and haircuts, Anna Wintour doesn’t need much of an introduction.

As the editor-in-chief of Vogue, artistic director of Condé Nast and long-rumoured inspiration behind The Devil Wears Prada’s inimitable Miranda Priestly (the book was written by Wintour’s former personal assistant, Lauren Weisberger), she’s become a bona fide fashion icon.

And thus, when I saw an opportunity to sit down with her for a one-on-one masterclass, I couldn’t sign up fast enough.

Wintour created the class, dubbed ‘How To Be a Boss’, in partnership with Masterclass.com—a digital collective of lessons taught by some of the world’s most influential and accomplished people. Tutors include Christina Aguilera, Margaret Atwood, Bob Iger, Wolfgang Puck, Serena Williams, Annie Leibovitz, Neil deGrasse Tyson and more, all of whom share stories, skills, shortcuts, failures, and successes within self-paced virtual classrooms.

As a concept, it seems to have gone down a storm. The trailer for Wintour’s class has been viewed over 21 million times on YouTube alone, and I was keen to see how the actual class would hold up against its evident appeal.

Minutes after subscribing, the notoriously private tycoon (and her trademark bob) waltzed onto my TV screen, pulling up a proverbial seat in her office, and got the ball rolling.

At roughly fifteen minutes long, each class offers bite-sized lessons with a lot of Wintour sound-bytes (a la “Florals? For spring? Groundbreaking”) and a lot of Vogue porn.

Starting with a peek ‘Inside Vogue’ (business and history-lovers, rejoice), the classes move into Editorial Decision-Making, The Power of an Image, Evolving a Brand, What It Takes For Designers to Succeed, and so on, all the way up to a congratulatory course-completion on Leading With Impact. With accompanying reading materials to inspire and push you at the end of each lesson.

Surprisingly, Wintour herself holds her post with benevolent confidence, teaching and sharing valuable business lessons learned from over thirty years at the helm of American Vogue.

Masterclass students are unprecedented access to editorial meetings, personal routines, and the cogs that turn the Met Gala—one of the fashion industry’s biggest and best annual fundraisers.

In fact, this very day marks Wintour’s 25th anniversary as Costume Institute chairman and organizer of the Gala, despite its untimely cancellation.

Essentially, it’s the most immersive fashion documentary I’ve ever watched. Albeit one with something practical to offer.

At £170 ($210) for an all-access annual pass to Masterclass, the single class doesn’t come cheap, but the intellectually curious are sure love exploring the other hundred-plus celebrity masterclasses currently available.

The full ten-lesson masterclass takes just over two hours to complete.