Out100: Caitlyn Jenner

Ryan Pfluger

Photography by Ryan Pfluger at her home in Malibu, Calif., on September 26, 2015. Styling by Grant Woolhead. Hair: Courtney Nanson. Makeup: Kip Zachary at Cloutier Remix. Dress by Diane Von Furstenberg. 

There couldn’t have been a more momentous year for Caitlyn Jenner than this one. She came out as transgender to Diane Sawyer in an ABC interview in April, revealed her new name and look in a Vanity Fair cover story in June, and was given the Arthur Ashe Courage Award at the ESPYs in July. Later that month, E! premiered I Am Cait, the docuseries that tracks Jenner’s life since coming out.

Between the accolades and praise, Jenner’s transition has been subject to a barrage of attacks and mockery from South Park, from right-wing media, from bigots on Twitter — to the degree that even Siri had to get involved, with helpful hints on how not to misgender the world’s most famous trans person. 

SLIDESHOW | Out100 2015

At her bright hilltop home in Malibu in September, Jenner is sanguine through all the fuss. “It’s my temperament” to be relaxed, she says. “But it is a lot.” Jenner is in a robe and slippers in a director’s chair, while a hairstylist and makeup artist prepare her for her first magazine photo shoot since that historic Vanity Fair cover. She flips between golf and football on the TV. 

“Yesterday was significant, because my name and gender change came through. Holy crap,” Jenner says, and takes a breath. “Here we are—honestly never knowing if this day would ever come. In some ways, it’s a little sad. Bruce was a good guy, did a lot of good things, raised a tremendous family and wonderful kids. But I just couldn’t play that game any longer.” She says the news was overwhelming. “I actually cried a little bit about it. I was on the golf course, off playing by myself. It was very exciting, but such a head trip.” 

While the first season of I Am Cait saw Jenner divulge private fears and depicted her exchanges with friends and family (some of whom had never before seen her present as a woman), the show also gave her the opportunity to discover her new community. She met with trans youth at a summer camp, with activists, and with many trans women, some of whom recounted their experiences as victims of anti-trans violence. So much of this world was entirely new to Jenner. Chandi Moore, one of Jenner’s new friends and guides, took her to task for too often saying “they” of trans people, rather than “we.” 

“I have been on the outside of that community, until four months ago basically. When did Vanity Fair come out?” Jenner says. “Like three months and a week,” says Ronda Kamihira, Jenner’s close friend and assistant who helped Jenner select her new name. “Chandi was absolutely right,” Jenner continues. “I’ve never, ever been able to talk to anybody. I didn’t meet my first trans person until I did the show. The only connection I had was watching YouTube videos. And during the ’70s and ’80s, and even through the ’90s, there wasn’t any of that. Just like anybody going through a transition, people find it hard to make the difference between ‘he’ and ‘she’ and gender markers and name changes. It’s tough for me to realize that finally, after all of this time, I’m part of the community. People want results right now. And all this stuff takes time.”

Jenner is acutely aware of the scrutiny she and her show are under, and she’s intensely concerned with getting it right. But rather than weigh oppressively on Jenner, her role and obligations have become a new mission in life. 

“I always thought that I want to wake up in the morning excited about the day, excited that I have things to do, things to accomplish, things to learn,” she says. “I want to be excited about life always. For the longest time, I was not. I isolated myself from the world. I never felt like I fit in anywhere. Today that’s all changed. I’m so terribly excited about the future. I have so many things to do. I feel like I have a place in life.” 

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Caitlyn Jenner

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