Caitlyn Jenner’s Vanity Fair Stylist Reveals Details From the Top Secret Shoot: “My Poor Office Thought We Were Doing Barbara Streisand!”

Caitlyn Jenner
Caitlyn Jenner's Vanity Fair stylist dishes on working with the transgender star Annie Leibovitz

Caitlyn Jenner’s style is “all-American,” Jessica Diehl, the stylist behind her now iconic Vanity Fair cover, reveals. In a new interview with VF Hollywood, the stylist opened up about dressing the transgender star for her big debut — which was one seriously top secret shoot.

“It was not easy,” the fashion guru admitted of keeping Jenner’s cover under wraps. “We couldn’t really prepare the way we normally prepare…. For this, I had to go into stores incognito…It was like Vanity Fair: Off the Rack,” she dished of Jenner’s looks, including her revealing cover, in which she donned a corset from Los Angeles’ Trashy Lingerie.

The shoot was so top secret that Diehl’s own coworkers weren’t even aware. “My poor office thought we were doing Barbara Steisand,” she admitted, laughing. “I just couldn't think of anyone tall. And I don't even know if Barbra Streisand is tall, but in my mind, she was tall. And so that just seemed right…We talked to no one,” she recalled. "Literally, the people here at Vanity Fair did not know. The entire fashion department did not know.”

While the shoot had to be kept on the down low, Jenner, 65, certainly weighed in.

“I went to go meet her before just to talk through what she wanted to do,” Diehl explained. “I went to her house and stayed there for a couple of hours maybe, and just spent the time talking through things and bringing up lots of pictures and inspiration images."

“She has certain ideas about what she feels great in,” Diehl said of Jenner’s “all-American” style. "But those ideas are still forming and taking shape. There will be some experimentation and trying things. Welcome to the world of women’s fashion! It’s not always smooth sailing, but I think she has a pretty good idea of what makes her feel good, and those are classic silhouettes.” In fact, just like Jenner’s model daughter Kendall Jenner, Diehl compliments the reality star on her “fantastic physique…She’s slim, and her proportions are very easy to dress.” 

While Caitlyn is still getting comfortable in her newfound skin, she’s open to experimenting with her looks.

“Classy and elegant is what] feels more comfortable to her. Not to say that she won't rock a sexy Roland Mouret number. She would love it. But there is definitely a more restrained feeling so far,” Diehl explained. “I think the most important thing here is that she gets to have fun and finally do things she's been wanting to do."

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