Caitlyn Jenner's Vanity Fair glamsquad reveals inspirations behind her look

Caitlyn Jenner, formerly Bruce, made a splash on Monday gracing the cover of Vanity Fair showing herself publicly for the first time. While the news of the transformation is still a buzz, the glamsquad behind the famous shoot is speaking out about how they carefully crafted Caitlyn's entrance into the world and how they kept it a secret.

"My poor office thought we were doing Barbra Streisand," stylist Jessica Diehl told Vanity Fair. "I just couldn't think of anyone tall. And I don't even know if Barbra is tall, but in my mind she was tall, and so that just seemed right!"



The preparations, which the magazine described as 'James Bond-esque' also included "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," added Jessica. "Three people in the fashion department knew, including me."

Jessica didn't have much time to style the shoot and wasn't able to put in the preparation she normally does for a cover shoot. "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 said. "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 Jenner revealed her new look this week Photo: Vanity Fair/Annie Leibovitz

Jessica visited Caitlyn at her Malibu home and the pair sought inspiration from vintage photographs of old Hollywood stars like Lauren Bacall and Faye Dunaway in The Thomas Crown Affair, as well as pictures of Jackie Kennedy.

When it came to the hairdo for the shoot, Caitlyn and famed hairstylist Oribe looked to Cindy Crawford’s hair for inspiration. “I wanted to create a glamorous look that I normally do for any woman, and sexuality was very important in this context," Oribe told Vanity Fair. "Bruce was one of the sexiest men alive, and I thought it was equally as important for Caitlyn to be a sexy woman.”

Caitlyn getting her hair prepped for the photo shoot Photo: Vanity Fair/Kathryn MacLeod

For the makeup, artist Mark Carrasquillo was careful to make sure Caitlyn looked her best. “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,” Mark explained to the magazine. “For me, I felt deeply responsible to represent what her goals were . . . She said, her whole life, looking in the mirror had different meaning and now, looking in the mirror (at the shoot), she felt more beautiful, and that was good enough for me.”


Bruce admitted in his 20/20 special that he enjoyed getting his nails done, so for the big reveal he donned a red manicure. “The color red was a statement throughout, and ‘Lady Is a Tramp’ was it,” manicurist Deborah Lippmann added. “And of course Caitlyn laughed when I told her the name of the shade.”


While the glamsquad worked to make sure Caitlyn looked perfect on the cover, the former Olympian thought hard about her name. "It's one of the hardest things in life – choosing your own name," she told Vanity Fair. The 65-year-old turned to watching pageants for inspiration and had the names Cathy and Heather as options before her assistant suggested Caitlyn. "I love that name, too," she said.

As part of the Kardashian clan, Caitlyn had to decide the spelling of her name and whether or not to start it with a "K." Ultimately, she decided against it as a way to fully embrace her new identity.

Next up, Caitlyn has to decide what to wear to the ESPY awards on July 15 when she will be honored with the Arthur Ashe Courage Award. She tweeted to her 2.2 million followers, "What the hell am I going to wear?"

From the looks of it, anything will look great!

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