Behind the Scenes of Caitlyn Jenner’s Vanity Fair Shoot: ‘We All Bawled Our Eyes Out at the End’

Though Caitlyn Jenner, 65, has developed a sense of her own style, when it came for her big high-fashion magazine cover debut, she had a little help behind the scenes from Vanity Fair stylist Jessica Diehl. Diehl shares tons of juicy backstage scoop in an interview at VanityFair.com, including how hard it was to track down the perfect cover look and what Jenner’s personal day-to-day style is like. Below, check out our top five discoveries, then read the rest here.

Caitlyn Jenner behind the scenes of Vanity Fair coverCourtesy Kathryn MacLeod


Number one style rule: Nothing tight or sheer that screamed ‘Kardashian.’
“And that is no disrespect to the Kardashian clothing choices at all. It’s just that [more elegant clothing] 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. Hopefully she’ll get to just have fun with it rather than have the fashion police judging what she wears every day. I think the most important thing here is that she gets to have fun and finally do things she’s been wanting to do.”


RELATED: Caitlyn Jenner’s Vanity Fair Cover Shoot: All the Scoop on Her Style, from the Gorgeous Gowns to Her Pin-up Beauty Moment

Due to the top-secret nature of the cover, Diehl’s staff thought they were shooting Barbra Streisand.
“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. 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.” (Adds Diehl on the prep: “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]. For this, I had to go into stores incognito … and buy stuff. That was actually what was fun. It was like Vanity Fair: Off the Rack!”)

But Jenner’s inspirations are more Old Hollywood-based.
“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, 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.”

Instagram Photo

She’s a fun model to dress — and she can thank the Olympics.
“I think she has a pretty good idea of what makes her feel good, and those are classic silhouettes. She has a fantastic physique. It’s just a totally well-taken-care-of physique. She’s an athlete, so the muscle tone is incredible. She’s slim, and her proportions are very easy to dress.

RELATED: Everything you need to know about Caitlyn Jenner’s inspiring journey

We should all take body-positivity lessons from Jenner.
“I’d like a slice out of that confidence pie. She was comfortable, confident, and has absolutely no reason not to be. 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.”

Are you surprised by any of Diehl’s reveals? Share below!

–Alex Apatoff
Follow @nicefunalex

RELATED VIDEO: 5 Ways Caitlyn Jenner Broke the Internet

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