The Education of Ms. Jenner

Photography by Ryan Pfluger

It was inevitable that Caitlyn Jenner would face criticism for not getting her very public transition exactly right. She has come out without knowing any other transgender people, and without having any point of reference for what it means to be publicly trans in the time of the transgender tipping point: using precise language, or towing a line regarding LGBT politics.

The consequence of being so new to the transgender community and the world of advocacy is that on her show, I Am Cait, the E! docuseries she executive produces, on which she tracks her transition, Jenner is often the stand-in for a cisgender audience member. She asks questions about the trans experience, sometimes makes assumptions and gets things wrong, and, then, hopefully learns something.

At her hilltop home in Malibu, Calif., Jenner is quick to extend me a hand, and instantly warm. Her gaze is direct. She retreats to the bedroom for a moment, where she’s having her hair and makeup done. “Come on in. Let’s do this,” she calls from the other room; it’s not a hallowed space, not an inner sanctum. In fact, her home, her bedroom, even her closet full of terrific new clothes, is a showcase for her new identity.

As often as she’s asking questions, seeking to learn about her community, Jenner is asked to explain herself — and that’s a tough thing for any newbie. But she’s getting up to speed quickly, employing the language of an advocate while deflecting notions that she’s speaking for anyone else.

“The media has kind of labeled me as the spokesperson for the trans community. That is not the case. I am only a spokesperson for my own journey. After that, I know nothing. Am I learning a lot? Absolutely.” She pauses. “I’m just trying to do my best, that’s all.”

One side of Jenner is so acutely aware of the potential for negative public opinion that it prevented her transition at least one time in the past. In the 1980s, Jenner was taking hormones and had cosmetic surgery on her nose. But the pressure of coming out in the public eye, when she was known as a paragon of athletic masculinity, the aura of Olympic gold still glowing about her, caused Jenner to wait. “I thought I would transition before I was 40. That was kind of my goal. I got to 39, I couldn’t do it.”

When she did come out in 2015 at age 65, those concerns still troubled her. “I’ve had such a phenomenally good life. I worked my ass off. I had tremendous respect from people,” Jenner says. “They respect what I did athletically and in my life and raising children.” Nevertheless, Jenner says she couldn’t escape certain thoughts: How are people going to think of you? Are you going to be viewed as a freak?

“All those things certainly go through your mind. But it’s natural,” she says. “You’re going from such a strong image — male, athletic, superstar, Wheaties-box iconic kind of stuff — and leaving that to go, quote, ‘to the weaker sex’” — Jenner makes air quotes — “certainly, I don’t see it that way. And although I really felt like I was doing the right thing, and I’m so happy that the response has been good, I was afraid I would really lose something in my life. But my main concern was really only my kids. I don’t want to do anything to embarrass them.”

The other side of Jenner is the one toughened to weather public denigration by years in the spotlight. “I went through a lot of struggles but came to the conclusion that it’s time. I can live authentically. I can handle anything,” she says. “I can take criticism. I honestly don’t have a problem with it. Just don’t criticize [my] kids that are dealing with this. From that standpoint, it’s been good. I never expected as positive a response as I’ve gotten.”

I confess to Jenner that I’m shocked at the positive response to her coming out as well. Chaz Bono had had a rough go of it at times, and most of the other prominent trans people, including Laverne Cox and Janet Mock, weren’t public figures until after their transitions. There hasn’t been a model for a transition with this level of scrutiny before.

“People appreciate honesty, OK?” she says. “Although it was difficult for me to be that honest, especially with the public, I really didn’t have a choice.”

In addition to the ignorant transphobia and cynical mis-gendering by the usual suspects on Fox News and in other conservative media, Jenner has faced critiques from within the trans community for overemphasizing the clothing and makeup aspect to her femininity, for being wealthy and white and privileged, and for actively seeking the mantle of trans representative.

And she’s faced ire from parts of the LGBT community for her political views, particularly for her onetime opposition to same-sex marriage, which she described on The Ellen DeGeneres Show, of all places. That’s a position she later changed by publishing a blog post on September 14, 2015, writing, “Like many people, there was a time when I didn’t realize how important it is for gay couples to have the right to get married. But after hearing from my gay friends and learning more about the hardships they faced because of discrimination, it became clear to me that everyone should be able to marry the person they love.”

A number of trans woman who appear on I Am Cait as Jenner’s roundtable of advisers, including academic Jennifer Finney Boylan, actress Candis Cayne, and activist Chandi Moore, have challenged Jenner on her assumptions about trans people — that being a woman is about the clothes or being with a man, or that poor trans women are milking government support systems for aid when employment is an ongoing crisis for trans people — and it has broadened her view of what it means to be marginalized in this world.

In November 2015, Jenner again took heat for declaring she’d be voting Republican in the 2016 presidential election. The declaration led to a variety of comments in the “not trans enough” and “traitor to the LGBT cause” vein, and to a confrontation with protesters in November outside a Chicago event at which Jenner had given a speech. “How dare you claim to represent us!” shouted one protester through a bullhorn.

Is it foolish to expect that Jenner would change her political stance after coming out? The world does include LGBT Republicans, after all. But she’s been challenged on her assumptions regarding marriage equality in discussions with actual gay people, and she came around to a more enlightened position. Jenner has already demonstrated that views do change. Yet in the discussion around her political conservatism, too few voices have acknowledged that freedom should include the freedom to express views that do not conform to a party line.

Caitlyn Jenner is very publicly learning what it means to be a woman, a trans woman, a trans celebrity — all under the watchful eye of news and entertainment media fascinated with her progress. In the most magnanimous of circumstances, the media are interested in her welfare; more prurient outlets want to know if there are any major missteps in her clothes, her makeup, her presentation as a woman. And while her look may be a small part of being a woman, it’s a big part of being a celebrity.

As I speak with Jenner she’s preparing for her first magazine photo shoot since the juggernaut Vanity Fair portfolio by Annie Leibovitz. The shoot is for Out magazine’s annual Out100 and for this story. Season one of I Am Cait has wrapped, and Jenner has some time to think. “What does this whole thing mean to me? There’s got to be more to this than just hair and makeup. Sorry, guys,” she says, turning to her hairstylist Courtney Nanson and makeup artist Kip Zachary.

Jenner continues: “There’s more to being a woman than hair and makeup. So recently, I’ve been trying to study up on it. My publicist’s assistant told me to read this book.” Jenner asks her friend and assistant Ronda Kamihira to bring over a book on the nightstand. It’s How to Be a Woman by Caitlin Moran.

“It’s actually very good and very funny,” Jenner says. “What I realized, when going through this book, is how my experience is so different than what a normal woman’s would be growing up — that’s obvious. The second chapter was about having your period. OK? I will never deal with that. So there is so much in life that I need to learn about who I am and be authentic with myself. But I never want to assume that this whole thing called womanhood, that I could ever experience all of that. I will be able to live authentically as female, but I’ve missed so much.”

Exploring the world as a woman can involve some of the most mundane activities, like golfing, or going to Starbucks, alone. “I’m so much more comfortable with myself now than I was four months ago. I’ve pretty much been out everywhere” presenting as she chooses, without a TV crew, without an entourage. But often not without the paparazzi, “which is a pain in the ass.”

Given her druthers, Jenner would prefer “a great pair of jeans and a T-shirt, and go to the market that way. And still look good. That’s ideal for me.” She says she’s watched her fashion icon family members’ sense of style over the years. She says she’d like to look good but not stand out. “Now, my family stands out. Love them to death, but their style is certainly different. And they’ve packaged it and sold it extraordinarily well. Better than anybody else in history, let’s be honest.”

“Kimberly [Kardashian West] says, ‘If you do go out, you’ve got to rock it, baby!’ ” Jenner snaps in the air. “You cannot let [the paparazzi] get that picture. They’ll take a picture of you with no makeup on, lousy outfit — and they’ll use it forever. You’ll never get rid of it. Kim’s very good at that stuff. It does take a little bit more work if you do go out. You’ve got to at least look good, at least the best you can.”

Jenner returns to the book: “But there’s more to life and womanhood than just that. And those are things I’m learning; I’m trying to read up on it. I’m trying to understand it because it’s all new to me.”

Jenner describes a dinner she had with Chandi Moore and Candis Cayne after season one of I Am Cait wrapped. “We’re sitting there and we go, ‘OK, what did we accomplish in season one?’ I personally feel that we opened up a conversation that for so long was swept under the rug. In so many ways like the gay issue, 20, 30, 40 years ago, people were sweeping that then. We’ve opened up the conversation. It’s OK to talk about trans issues.” Jenner leans back in her chair.

She speaks with the air of a new convert, and it’s an attitude of pioneering conveyed by many new warriors in an equal rights struggle. On her blog, Jennifer Finney Boylan captures the tenor of some reactions by prior generations of trans activists who feel that Jenner should be joining the procession, not leading the parade: “Many of us feel like, well goddamn it, we are the ones who deserve to have our own show; we are the ones whose stories ought to be told; we are the ones who ought to have purty pictures of ourselves taken by Annie Leibovitz. And of course, we are right…Caitlyn Jenner has been able to reach people the rest of us might not have been able to reach. She is not the perfect ‘spokesperson,’ assuming that such a person could ever exist — given the contentiousness of our community, and its vast diversity…What she wants is to try to do good in the world, and I think she is succeeding.”

“You cannot believe the stories that people have come up and told me over the last four to five months. I mean, unbelievable,” Jenner says. She hears stories of friends, families, kids, and “a lot of mothers. This conversation never would have happened if I had not told my story. And that makes me feel good.”

Jenner returns to a tone more in keeping with a practiced giver of speeches. “You cannot believe the people that I have met. It’s in every walk of life, some hiding in the shadows, some not. This is a human condition. It’s not just here in the U.S. It is everywhere.” Though this may be a familiar mode, perhaps after so many years of giving inspirational talks about her 48 hours in the Montreal Olympic Stadium, it’s not rote. It’s heartfelt.

Jenner says that after too many years feeling aimless, she wakes up with a mission in life, to promote the welfare of transgender people. She won’t let the opportunity pass to share her message, that there are so many problems facing the transgender community, many she’s just coming to learn about. “To see that it’s just — it’s gut-wrenching. Suicide rates, murder rates. We’re up to 20 murders [to date in 2015]. The hatred. There’s just so much work to be done,” she says. “I am certainly the exception to the rule. I am not the rule.”