How did Vanity Fair’s Jessica Diehl Pull Off Caitlyn Jenner’s Shoot?

by Eddie Roche

Vanity Fair

Sure, Caityln Jenner was yesterday’s hot topic due to her epic Vanity Fair cover (aka the best kept secret in media history), but everyone was also wondering: How the hell did the VF fashion team pull that off? “Normally we go to Valentino or Armani, and say we are shooting a cover and ask if they can give us some clothes [to borrow],” VF‘s Jessica Diehl told “For this, I had to go into stores incognito, so to speak—not like anyone would know what I looked like anyway—and buy stuff. That was actually what was fun. It was like Vanity Fair: Off the Rack.”

So, what did Diehl tell her very own staff? “Well, my poor office thought we were doing Barbra Streisand!” she says. “I just couldn’t think of anyone tall. [Laughs] And I don’t even know if Barbra Streisand is tall, but in my mind she was tall. And so that just seemed right. I should have said Rene Russo, who I think [Caitlyn] looks like more anyway. The secrecy, I have to say, had a lot to do with being discreet and shopping—a lot of which we did online. 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 also notes that Jenner was surprisingly cozy in her own skin at the shoot. “She was comfortable, confident, and has absolutely no reason not to be,” she says. “It was probably the most exciting thing to see—there was real joy in her feeling comfortable and happy in her skin. It was amazing. I don’t usually get super-sentimental about things, but that was probably the most emotional and open experience I have ever had on a shoot.” Read more at


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