Caitlyn Jenner’s Photo Shoot: How Vanity Fair Kept It Under Wraps

“The people here at Vanity Fair did not know,” the magazine’s fashion director reveals about the top-secret interview

Kathryn MacLeod/Vanity Fair

One image and one alone channeled Caitlin Jenner’s momentous coming out, so getting it right was vital — as was keeping it secret. Misdirection, subterfuge and (gasp!) actual shopping were all unusual parts of the production process.

“Normally we go to, I don’t know, Valentino or Armani, and say we are shooting a cover and ask if they can give us some clothes (to borrow),” said Vanity Fair’s fashion and style director Jessica Diehl in an interview on the magazine’s website. “For this, I had to go into stores incognito … and buy stuff … It was like Vanity Fair: Off the Rack.”

The ruse wasn’t only limited to high-end retailers.

“My poor office thought we were doing Barbra Streisand! … I should have said Rene Russo, who I think [Caitlyn] looks like more anyway … We talked to no one. Literally, the people here at Vanity Fair did not know. Three people in the fashion department knew, including me.”

Diehl met with Jenner to talk through the shoot. Vanity Fair’s “is a very specific look,” she continued. “But we also just wanted to talk about her style in life … we sort of thought that the nicest thing to do was to focus on style over fashion. Nothing too bling or too shiny.”

“That is no disrespect to the Kardashian clothing choices at all. It’s just that feels more comfortable to her,” Diehl said. “There was a stripped-down idea there that sort of felt like underneath all of this excitement and newsworthiness is the soul of a woman.”

Diehl brought Jenner loads of pictures and inspiring images, “from Lauren Bacall to ‘The Thomas Crown Affair’ to people who I think look amazing on the red carpet. And just vintage photographs of Old Hollywood stars. A couple of Jackie Kennedys are never wrong.”

She said Jenner is “all-American in so many ways” with a fantastic physique. “She has certain ideas about what she feels great in. 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!”