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To dress Caitlyn Jenner for her top-secret debut Vanity Fair magazine cover, fashion and style director Jessica Diehl had to go undercover. Diehl spoke to the New York Times about how she pulled off the cover shoot, saying that instead of calling in looks to designers, she went shopping both online and in stores like Bergdorf’s, Barneys, Max Mara, Tom Ford, Michael Kors, and DVF. Only 10 people at the magazine knew about the shoot; everyone else though they were shooting Barbra Streisand.
Jenner didn't get to try on a single look until the day of the shoot, but everything Diehl bought fit the 6-foot-2 Jenner. "That actually never happens to me," she said. "The physique is really extraordinary. We should all be decathletes."
Before the shoot, Diehl met with Jenner to learn about Jenner's personal style and her inspirations for the cover. They decided on classic all-American style, drawing inspiration from icons like Lauren Bacall and Jackie Kennedy.
Jenner even kept a Donna Karan dress from the shoot, as a gift from the magazine. "That was probably, to me, the most important thing, that Caitlyn feels good about everything," Diehl told the Times. "There would have been no way that I would’ve persuaded Caitlyn in a moment like this — which I can sometimes do, persuade an actress to wear something that I really want her to wear," she said. "This was not the moment for that."