On the evening of May 2, Anna Wintour will take her place at the top of the carpeted steps leading into New York City’s Metropolitan Museum of Art. Wintour, now Condé Nast’s global chief content officer as well as the global editorial director of Vogue, has been hosting the Met Gala for nearly 30 years. She is always happy on this night, a year in the making—but this is still work. And that means every detail must be perfect.

Former Met Gala planner Stephanie Winston Wolkoff—also a former adviser to Melania Trump—describes Wintour as “militant” during the party each year. “Where is everybody? It’s time,” Wintour says to her team. “Where are they? Can you tell me where they are?” The Vogue…