Caitlyn Jenner’s Photo Shoot: From the Top-Secret Preparations to the Celeb Who Inspired Her Hair

Mashable says the magazine took many precautions to pull off their Monday coup. The photo shoot at the VF editorial office was top secret, and the story and pictures were laid out on a single computer that was not connected to the internet. All assets were transferred to a thumb drive each night and deleted from the computer.

The article was reportedly hand-delivered to the printer!

Diehl's Bond-esque preparations included telling the staff they were preparing for a Barbra Streisand shoot! “I just couldn't think of anyone tall,” she told VF.

It also meant shopping online and secret trips to the store. “We talked to no one. Literally, the people here at Vanity Fair did not know. Three people in the fashion department knew, including me.”

“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],” she told VF. “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.”

Caitlyn's debut, in an ivory corset from Hollywood's Trashy Lingerie, wasn't about being risqué, it was about “honesty and purity,” said Diehl.

“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,” she explained. “And that didn't need a lot of covering up. It was not meant to be risqué in any way. It was really meant to sort of show with all honesty and purity, “This is what is going on. Here I am.”

The inside pages are filled with beautiful shots of Caitlyn, taken by photographer Annie Leibovitz.

“Everything looks good on her. That just doesn't happen. It was never the clear forerunner — it just kind of became clear when we spent the day together. Annie, I am sure, had it in her mind [what the cover was going to look like] way before. Annie always has the thing in her mind way before and lets it all unfold, and then we all take credit for it. The off-the-shoulder Zac Posen was really beautiful. But then, all she really wanted to do was be open and honest. That is how that look felt.”

Also helping with the look… Caitlyn's glam squad! Makeup artist Mark Carrasquillo, hairstylist Oribe, and manicurist Deborah Lippmann.

Carrasquillo explained, “I didn't want her to look like a man in a dress. I wanted her to look like a beautiful, 65-year-old woman.”

The artist turned to his arsenal of beauty products, including Tom Ford Traceless Foundation SPF 15, Eve Pearl Salmon Concealer, Estée Lauder More than Mascara in Rich Black, Tom Ford Eye Defining Pen in Black and Sculpting Powder by Kevyn Aucoin in Medium.

He also used several Serge Lutens products like a peachy blush called Shade No. 2, a lip pencil and finishing powder.

In one photo Caitlyn wore a pop of Jungle Red by Nars on her lips.

It turns out her hair was actually inspired by Cindy Crawford!

Oribe revealed, “We looked to Cindy Crawford's hair for inspiration, which is always glamorous but natural-looking," Oribe explained. “I wanted to create a glamorous look that I normally do for any woman, and sexuality was very important in this context. Bruce was one of the sexiest men alive, and I thought it was equally as important for Caitlyn to be a sexy woman.”

He used Dry Texturizing Spray for volume and Signature Royal Blowout Heat Styling Spray for shine and softness.

Lippmann added, “Looking back on my career, this shoot was historic on so many levels, because I realized how important nails are to transgender women… nothing compared to this cover. It opened my heart, and it opened my eyes, and I feel so blessed to be a part of it.”

The chosen color? Lady Is a Tramp from Lippmann's own line. “She was so happy to be a girl, and she was so at ease. Her attitude was very much, 'Let's do it!,' and she enjoyed every moment of it.”