CO VER STORY
Caitlyn Jenner speaks candidly about her double life as Olympic athlete Bruce, and the joy of finally being the woman she always knew she was
Iam at the Marriott hotel in Orlando giving The Speech. The same words, the same message, the same title, and the same feigned enthusiasm – just like the hundreds of other times I have given it all across the country.
I know why people are here in the audience. They have come to listen to the Bruce Jenner who won gold in the decathlon at the 1976 Olympics in Montreal and was dubbed ‘the world’s greatest athlete’. The Bruce Jenner who became, overnight, an American hero. The Bruce Jenner who is the essence of virility and the ultimate conquistador of women. The Bruce Jenner who gets anything he wants. The Bruce Jenner who looks at himself in the mirror and sees a stud among studs.
They don’t know that when I look in the mirror I see something entirely different, a body that I fundamentally loathe: a beard that is always noticeable no matter how close the shave; a penis that is useless except for pissing in the woods; a chest that should have been breasts; a face with a jawline too sharp and a forehead too high. They don’t know that, contrary to what they imagine, I have slept with five women in my life and I was married to three of them.
They only know what they see, which is the image I have carefully cultivated over decades, which in turn is the image the media has bought into because it’s the irresistible story they want to tell: the Olympian who rose out of nowhere and was the son of a tree surgeon, who married his college sweetheart, who spent almost half his life working to win that gold medal. In doing so I have also come to represent, perhaps more than any other athlete of modern times, the America of hard work and realising your dreams.
They know what they want to hear: a life defined by those two days at the Olympic stadium when I broke the world record and ran around the track waving a small American flag handed to me by an adoring fan. They don’t know that underneath the dark blue business suit I am wearing panties, a bra and tights. They don’t know that I am not Bruce Jenner, but a woman I will come to call Caitlyn; a woman who still has to be Bruce, except for stolen moments here and there, 20 minutes or an hour where I can feel what it is like to be my authentic self.
Imagine denying your core and soul. I am glad that you probably can’t, because you don’t really live. You just try to get by, pray that the conflict inside – it won’t go away completely; you tried that already and it won’t – will maybe take a breather, move to the background of your mind instead of the foreground.
Those in the audience don’t know that I am always uncomfortable. I am acting here because that’s how it has been almost all my life. I am playing Bruce because that’s what people listening want. That’s what society wants. I get paid a lot of money for it.
I finish The Speech. I do the usual meet and greet afterwards. I fake my way through by talking sports with the guys and making small talk with the women because I cannot relate what is in my heart. All I really want to do is go up to my hotel room because it is only on the road that I can feel any self-fulfilment: my wife Kris will not permit any of this behaviour at home, just like my two ex-wives, Chrystie and Linda. She doesn’t want to see it or deal with it, so we never talk about it. Why would she? She fell for Bruce Jenner, not some porcelain doll knock- off. They all did. I wasn’t totally honest with any of them. I was too ashamed, too scared. But it was more than that. Just like my ex-wives, I couldn’t conceive of it either.
I lock the door to my suite at the hotel and put on the ‘do not disturb’ sign. I order room service – a tuna sandwich and a Diet Coke – and tell the waiter to just leave the tray outside the door. There are several mirrors in the suite and a make-up mirror in the bathroom, which I like. I’m in business.
The ritual actually begins before I even get to the hotel. It starts at the airport, where I have taken every possible precaution I can think of to get through security without incident.
Nobody enjoys packing, but try packing for a man and a woman. I have a female friend who buys clothing for me since I am too scared to do it myself. I tell her what I need and she looks for it. Given that I am six feet two inches tall, it’s hit and often miss. Shoes are particularly tricky because of my big feet. The selection is further ➤
People want Bruce: the world’s greatest athlete, the American hero, the essence of virility
➤ limited because I assiduously avoid high heels: the last thing I need is to be taller.
I layer the outfits I am going to wear at the bottom of the case, then I stuff a wig inside the sleeve of one of the garments and fold it over for extra precaution. I put my dark blue business suit on top, along with assorted shirts and underwear. If I am stopped and my luggage is searched I can always say that I packed for both my wife and me. I have an excuse ready for any situation. Always think on your feet.
I always bring a box of clear plastic wrap, which, in my own homegrown method of feminisation, I cinch tightly around my waist to heighten my hips and buttocks. And let’s not forget the little tube of glue that I use to do a makeshift facelift.
Fortunately I have gone to the bathroom before airport security to remove the breast prosthesis I am wearing. I forgot once and the alarm went off as I went through the metal detector. As the officer positioned his wand on my upper chest, I was convinced the detector would pick up something on the bra. I braced myself for being marched to a private room to remove my shirt. The fear was palpable until it turned out the wand had picked up a zipper on the rain jacket I was wearing. I was more careful after that.
At the hotel, I unpack and lay the clothing I will wear on the bed. Because I am not one to experiment in this situation, two items are almost always the same. One is a black dress with spaghetti straps that falls just above the knee, because if I know anything about myself, it’s that the legs work. They have always been thin. I can’t say the same about my arms – definite no show – so the other item is a black jacket to hide them.
I stole these clothes from Kris’s wardrobe because they are quite big and I did not think she would notice them missing. (By the time she discovered I had been ‘borrowing’ them for several years, they had been stretched so much she did not want them back anyway.) It is my go-to outfit – cute but not too formal, black because, as we all know, black makes you look thinner. I have stolen make-up over the years not only from Kris, but also from the rest of the K-troop: Kourtney, Kim and Khloé, and eventually Kendall and Kylie, because – trust me on this – there is more make-up per user in our home
I have been acting almost all my life. Imagine denying your core and soul
than any in history. Applying make-up is always intense and I sometimes think I work harder on it than I did to win the decathlon. I secretly bought how-to books since there was nobody to help me. I keep the books, along with my meagre collection of clothing, in a small locked closet in the back of my wardrobe. Kris and I have negotiated this, since she is terrified, as I am, of the kids finding something.
The eyes are the most important, because they are, of course, a window into the soul: get the eyes right and everything else follows. They come out fine; I am definitely improving. But sometimes I get overconfident, and here I am, ‘the world’s greatest athlete’, with my hands shaking, trying to put false eyelashes on, which only results in my getting black glue all over my eyelids.
I look at myself in the full-length mirror. I walk back and forth several times to make sure I am passable enough as a woman. I carry a handbag – Kris’s, of course, which is a little harder to borrow since she started keeping better track of her things. I leave the room. I usually take the stairs to the lobby to avoid getting stuck in the lift with other guests. But I am on a high floor and don’t want to leave looking like a mess, so I use the lift. I don’t say a word because my voice, singsong and a little high-pitched, will give me away instantly after so many years in the public spotlight. I turn my back as if I am disinterested, a stuck-up broad, and bend my knees a little to not look too tall.
I leave the lift and walk around the lobby for 20 minutes, not a very good return on investment, since it took at least an hour to get dressed. It’s exciting, and I sometimes wonder if that is my driving force. (Living with the Kardashian women is incredibly rewarding, don’t get me wrong. They are dazzling, and in several years’ time, Keeping Up With the Kardashians will draw millions of viewers worldwide. I come across in the reality show as a well-meaning but slightly doddering patriarch, who has no life of his own and is subsumed by the women who surround him ➤
➤– a totally true depiction.) I walk to the end of the lobby and then turn around and go back to the hotel room. I never linger. I never stop. I never go to the restaurant. I look for remote crevices and corners. I try to avoid eye contact as much as possible, although I am acutely aware that I am being checked out.
I am not too worried about being recognised, because even if someone thinks they see Bruce Jenner in a dress (which they did), nobody would believe it because Bruce Jenner is the last person you would ever expect to be wearing a dress. What concerns me is whether or not I am presentable. The length of the glance is the key determinant: a quick look means no big deal, it’s just another woman. A longer one worries me, the implication being, ‘What the hell is that?’ Sometimes I think I look pretty darn good. Other times I feel like a thinner version of Big Bird, standing out for the world to see and snicker at after I pass.
I remember how once in another hotel a man came up to me in the lobby. I was convinced this was it – busted. Instead he smiled and handed me a rose. I returned the smile and got away from him as quickly as I could. The last thing I wanted was a conversation. In the dozens of outings I have made to hotel lobbies over the years, I have never had a conversation with anyone. But I was flattered.
I leave the hotel, get into my rental car and drive around for an hour or so. I park the car on the outskirts of a shopping mall, as far away as possible from any security lights. I walk around for a little bit, holding the keys in my hand in case of an unexpected encounter that requires a quick dash back to the car. Thank God I am wearing sensible shoes. I do not stay out for very long, but the freedom of walking around in a car park is momentarily liberating. It is incredibly exciting: the pulse quickens, the heart rate rises, a combination of giddiness, confidence and daring the world – and happiness, sublime happiness.
I am still feeling good about myself when I get back. Nobody suspected anything. But I have an early flight tomorrow, which means Bruce will be back, rise and shine. I sleep with the make-up on and it smears all over the pillow.
Outwardly, my life is good: I have terrific children, a strong marriage (at least before Keeping Up With the Kardashians took off), steady work and a public that likes me. But it is not enough. It will never be enough. At this point in my life – the 1990s, I’m in my 40s – I honestly don’t think I will ever get that peace in my soul. Concerns over family and the strictures of society are just too great. I seriously think about putting a stipulation into my will that I be buried as a woman. Maybe that’s the best and only answer: to die the woman I always was, wearing what I had always wanted to wear (for more than 20 minutes in a hotel lobby or driving around aimlessly).
That’s the way I want to go to heaven. I yearn for the answer here on earth. But until I find it, I do what I do best. I play Bruce.
***** I watch the TV interview at the home in Hidden Hills, Los Angeles, where Kris and I once lived together. All the Kardashian kids are here, with the exception of Rob. Kendall and Kylie are on a sofa in the living room. Kris is sitting behind us on a chair. How shocked or not she is by my transition is immaterial at the moment: it has to be very, very weird to see your former husband of 23 years, with whom you have two children, go on television in front of an estimated 17.1 million people and say: ‘For all intents and purposes, I am a woman.’
Wow. I can’t believe I just said that. I am a woman.
Do you know how incredible that sounds, how I never thought those words would come except in moments of beautiful privacy with a handful of others?
The secret is out after 65 years. Say it again to the heavens so God can hear it and smile. I am a woman!
Kendall and Kylie, who between them have more than 200 million followers on Instagram and Twitter, start hitting social media almost immediately after the interview has begun. Their sisters join in.
Kendall gives the initial results: ‘Dad, you should see the reaction you are already getting, it’s incredible.’ It’s a great moment. I go over to my daughter Casey’s [with first ➤
I wasn’t totally honest with any of my wives. I was too scared, too ashamed
➤ wife Chrystie Scott] house in Santa Monica and make it in time to watch it again at 9pm. All the Jenner kids are there with their spouses and significant others, as well as my ex-wives Chrystie and Linda. They, too, are elated with how the TV show went. Everybody in the three families is happy. At least for a day.
Several of the Jenner children were interviewed during the show, as were my mother and sister. The Kardashian side feels slighted by their noticeable absence. They are right to feel this way. They were slighted on purpose because of the research showing that any time a Kardashian is on television, many people think it is a publicity stunt to make money.
I love my kids and the last thing on earth I want is for them to somehow think I am rejecting them. But I needed to build a wall and distance myself for this interview. It was too important. After all the time it has taken to get me to this point, I needed to make it clear that this was real, my life, and not some publicity stunt. I couldn’t afford to add fuel to the rumour that I was doing it for the money. I had just one chance. This had to be about me and only me. If I screwed up then at least it would be on my own terms.
Much to my relief, the public reaction is phenomenal. My honesty and sincerity have come through, no doubt because I only have one advantage: I know how to be candid, regardless of the repercussions. The level of interest was amazing, too: it garnered ABC show 20/20 its highest ratings for more than 15 years.
I have made it through whole. I am still in one piece. But I’m not quite done yet. Wait until they see Caitlyn for the first time.
Everybody has advice about what I should wear for the Vanity Fair photo shoot. The older Jenner children want me to tone it down – elegant but not too flashy or revealing. Their intentions are good: they want me to set the right tone of womanhood as they define it. They are also sincerely worried that the more glam I try to be, the more I will feed accusations of exploitation. They are trying to protect me. But their vision of womanhood is not my vision of womanhood.
The most resonant advice comes from Kim, who, as she points out, doesn’t simply know fashion but is fashion: ‘You gotta rock it.’
Several weeks before the shoot, the photographer Annie Leibovitz comes to my house to scout the site and get to know me a little better. Vanity Fair’s fashion and style director Jessica Diehl flies out from New York to meet me as well and find out what I like and what I don’t – or, more accurately, what I shouldn’t wear, tactfully steering me away from big fashion
The reaction to my interview is phenomenal. But I am not done yet. Wait until they see Caitlyn
statements in favour of a mix of what she describes as Rene Russo in The Thomas Crown Affair meets Angelina Jolie, elegant with a dash of tough.
The day before the shoot, she and fashion editor Ryan Young visit for a fitting. I had always fantasised about having beautiful clothes that fit. As many times as I had stood in front of hotel mirrors and thought I looked good, I always knew it could be better, but I had convinced myself I would never get the opportunity. So now…
Some things have been shipped previously, others were brought by Jessica and Ryan. There are well over 100 different pieces: gowns, blouses, sweaters, belts, cocktail dresses, lingerie, jewellery, high heels. So many items that a tent is put up on my deck.
What is perhaps most amazing of all is that none of the haute couture shops where Jessica and Ryan searched for clothing in New York asked who exactly these items were for, given that the person was six foot two.
Jessica thinks I have the look of a 1980s Amazonian model – which is what I may want carved on my tombstone, along with a quote from her saying I look perfect in Tom Ford.
I initially have trouble believing that this is all for me to try on, the only goal being to make me look my best. Ninety per cent of the clothing fits. It is the first time I have ever openly tried on women’s clothing in front of a group of strangers. It is so easy, so natural, so effortless, so much fun; the way my life was always supposed to be.
The shoot lasts for two days: Annie Leibovitz is Annie Leibovitz, after all. She has a clear vision of how she wants me to look: a little bit 1940s Hepburn, a little bit Vargas girl; glamorous and beautiful with a touch of sexy. The photo of me that is chosen for the cover, posing in a cream bustier with perfect make-up and hair and a headline that simply says ‘Call Me Caitlyn’, will become instantly iconic. It is the photograph that everyone will remember me by.
But the photo I remember the most takes place in my garage, which has been converted into a studio. I am wearing an off-the-shoulder black gown by Zac Posen. It is a killer, if I do say so myself. All the lights in the garage have been turned off, leaving only the ones set up for the shoot. There is darkness everywhere except for on me, a spotlight effect. There is a large mirror. Annie tells one of her assistants to move it behind the camera so I can see myself.
Not every day of my life will be spent with hair and make-up done, wearing beautiful clothing handpicked by a stylist, with Annie Leibovitz taking my photograph. In fact, it is safe to say that no day of my life will ever be spent this way again. But in that moment when I look in the mirror, I truly see myself for the first time. So many other times I have looked in the mirror with a familiar loathing and disgust.
But now – now the view from the looking glass is different. I see who I am. I am who I know. I know who I am. I am Caitlyn. Caitlyn Marie Jenner. Forever forward.
It is so easy, so natural, so effortless; the way life was supposed to be