"The First Monday in May" offers a captivating look into the world of high fashion and art, as it chronicles the preparations for the Metropolitan Museum of Art's annual fashion exhibition and gala. The documentary takes place during a year of unprecedented access to the Met's Costume Institute, and follows celebrated curator Andrew Bolton as he works tirelessly to create an exhibition of Chinese-inspired Western fashions. With the help of Vogue editor-in-chief Anna Wintour and other fashion luminaries, Bolton delivers what becomes the most attended fashion exhibition in history. Throughout the film, Wintour's daily life is also showcased, raising questions about the intersection of fashion and art.

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Sommige films met vergelijkbare genres en die rond dezelfde tijd als The First Monday in May zijn geproduceerd, omvatten Tickled, Iris, The Wonder of Dogs, My Octopus Teacher, David Foster: Off the Record, The Kids Menu.