Former Olympian turned transgender icon Caitlyn Jenner bravely unveiled her new image to the world this week on the cover of Vanity Fair. The stunning portrait, captured by Annie Leibovitz, was evocative of old-Hollywood glamour—a look that had many recalling Lana Del Rey and Jessica Lange.
So, who was the woman behind helping Jenner present her fresh female prowess for the first time? Vanity Fair style and fashion director Jessica Diehl. In an interview with the New York Times, Diehl provided more details about the photoshoot’s fashion direction and keeping the entire project a tight-lipped secret.
Considering this was Jenner’s first official opportunity to manifest her feminine fantasy, Diehl said the biggest challenge was pulling together a look that made sense. “It was really about finding out from Caitlyn what this all means to her,” she said to the NY Times. The two referenced icons like Jackie Kennedy and Lauren Bacall, and pulled together an array of top brands, including Diane Von Furstenberg and Donna Karan.
Keeping this entire ordeal a secret was obviously a major hurdle for Diehl’s production team, considering the grand amount of press surrounding Jenner’s transition. While a “skeleton group” knew the subject would be Jenner, the rest was led to believe they were planning a Barbara Streisand shoot. Because of this, Diehl said she was forced to personally shop for clothes, rather than have designers send samples for Jenner.
On set, there was a no phone policy. “They were all in a box,” Diehl said. “There was nothing.” Rather than using Vanity Fair‘s go-to locations and props, they had to shoot Jenner at her Malibu home, again to ensure total privacy. “Luckily, she has some pretty fierce cars, just in the driveway,” Ms. Diehl said. “We didn’t have to go anywhere.”
Although Diehl admitted it was tricky finding womenswear in sizes that’d flatter Jenner, who stands 6-foot-2, the Vanity Fair editor said Jenner’s proportions were made for fashion: tall, slim and narrow-hipped. And even without having the luxury to fit Jenner in the clothes prior to shooting, Diehl said the pieces she pulled all fit beautifully. (Kudos to Diehl’s talent and kudos to Jenner’s Olympian bod)