Entertainment Love and Romance From Bruce to Caitlyn: Photos of Jenner Over the Years Share PINTEREST Email Print Love and Romance LGBTQ Relationships Sexuality Divorce Teens Friendship By Julyne Derrick Contributing Writer Texas Lutheran University American University Julyne Derrick is a freelance beauty writer and contributing writer for Byrdie. our editorial process Julyne Derrick Updated August 20, 2019 01 of 33 Photos Featuring Bruce Jenner's Transition to Caitlyn From Bruce Jenner (in 1981) to Caitlyn Jenner (in 2014). Getty Images by Michael Ochs Archives; Annie Leibovitz for Vanity Fair Editor's Note: Bruce Jenner came out as "Caitlyn Jenner" in a Vanity Fair magazine cover story. He revealed his plans to transition into a woman in an exclusive interview on April 24 with Diane Sawyer. "Yes, for all intents and purposes, I'm a woman," Jenner told Sawyer. This slideshow shows Bruce Jenner's transformation over the years from Olympian to a friend of Hollywood royalty to a member of the Kardashian family and finally, to the solo life where he's transitioned into a woman named Caitlyn. But first, before we lap up the pictures, let's have a frank talk about what you are about to see. We all know the tabloid world had been watching eagerly for years for signs that Jenner, 65, was transitioning into a woman. Look closely at the pictures in this gallery and perhaps you will spot signs that are relatively small (facelifts, a nose job or two, hair and nails grown long, a divorce and a surgically shaved Adam's apple). When added up, these small signs become a rather clear, bigger picture: Bruce Jenner was becoming a woman. What was once an intrusive tabloid story suddenly morphed into the legitimate news in the winter of 2015 when Jenner's mother reportedly confirmed to RadarOnline.com that Bruce was transitioning from male to female. Although Bruce did not confirm this and refused interviews with media, the mainstream press, including The New York Times, began covering the story in early February. And then Jenner confirmed those rumors on April 24, telling Sawyer he has the soul of a woman, that he will remain "Dad" to his kids, but that from here on out, he is no longer Bruce Jenner, but "her." Pronouns, after all, are very important to the transgender community and Jenner was not yet ready to share a chosen new name. And then, the bombshell — Bruce's coming out on the coveted cover of Vanity Fair magazine with a three-word headline, "Call Me Caitlyn." Perhaps as a final breaking off from the Kardashian family, Jenner chose a name that began not with a K, but with a C. Her story was reported by Buzz Bissinger with photos shot by the iconic Vanity Fair photographer Annie Leibowitz. The Jenner-Kardashians have never shied away from baring all for public consumption, and Bruce Jenner was the patriarch of the family (though he was overpowered by the clan matriarch, Kris Jenner). We, the public, have lapped up every morsel the Kardashian-Jenners have thrown to us. We've watched them court, marry, divorce, abuse alcohol, retreat into rehab, struggle to lose weight, break into modeling, and get pregnant. We've gone on their vacations, into their delivery rooms — several of them — and we've even been invited into the intimate confines of a fertility doctor's office. Vaginal ultrasound on TV? No problem! Let's do two at once, thanks for the invite, Kim, and Khloe! And breaking news alert, on the day that Caitlyn's magazine cover was announced, it was also announced that Kim and Kanye were expecting their second child. Coincidence? But wait. Stop. Silence the snickering. Turn down that Kanye album. Throw a blanket over the glitz and glitter. Sit down, please, and rest your Manolo-clad feet. The mood has shifted. It's now respectful. The mainstream media has torn from your hands the tabloid with Jenner's feminized head morphed onto the body of a woman and replaced it with this headline: Bruce Jenner’s Courage. We are invited on a public journey like one we've never seen before. How many of us know a transgender person? Have we heard their stories? Listened to their struggles and celebrated with them their inevitable triumphs? Now we get to. Jenner told Sawyer he was making his transition public in an effort to help other transgender people for whom the world can be a very lonely place. In honor of Jenner's brave transition, view photos of her life. You'll see her as a proud Olympian, a doting father, a golfer, a race car driver, and a husband. You will witness those small clues of her transition, the ones the tabloids exploited. You'll see her taped neck, her red fingernails. Moments meant to be private but that were captured by a paparazzi lens. Jenner's brave journey is now public. She is simply becoming the person she was meant to be. As Jenner said herself, the person she is. CNN reports that GLAAD CEO Sarah Kate Ellis said in a statement, "Today, millions of people learned that someone they know is transgender." She said Jenner's story "will impact and inspire countless people around the world." Good. 02 of 33 Bruce Jenner in July 1976 at the Olympics Tony Duffy/Allsport for Getty Here is the iconic photo of Jenner celebrating after his record-setting performance in the decathlon at the 1976 Summer Olympics in Montreal, Canada. Jenner won the gold medal in the decathlon, setting the world record of 8,616 points. His world record was broken in 1980. According to Jenner, he overcompensated with his confusion over his gender by focusing intensely on athletics. “For all intents and purposes, I am a woman,” he told Diane Sawyer in an interview. “People look at me differently. They see this macho male, but this female side is part of me, it’s who I am. I was not genetically born that way.” 03 of 33 Bruce Jenner in 1979 with Actor James Brolin Photo by Joan Adlen/Getty Images Here, he chats with actor James Brolin in April 1979 in Long Beach, California. Bruce was a race car driver for a brief moment in the 80s. He said that even as a woman he expects he will still love his traditionally masculine pursuits, such as racing and flying. 04 of 33 Bruce Jenner in 1981 with Wife Linda Thompson Photo by Frank Edwards/Fotos International/Getty Images Here, we see Jenner and his wife, Linda Thompson, pictured in October 1981 in Los Angeles. He married Thompson in 1981, but they were separated by 1986. Jenner has been married three times and has six children. Jenner told Diane Sawyer that he wasn't as honest with his wives as he could have been. He basically downplayed his gender struggle and led them to believe he liked to cross dress and wear makeup on occasion. When he finally came out to wife Linda Thompson and admitted he wasn't sure he could remain a man forever, it broke up their marriage. Linda went on to marry David Foster, the music producer currently married to Yolanda Foster on "The Real Housewives of Beverly Hills." 05 of 33 Bruce Jenner in 1985 with Nancy Reagan and Cher at the White House Photo by Pictorial Parade/Getty Images Jenner acted in a few movies and TV shows in the 80s. Here's a photo of Jenner with First Lady Nancy Reagan and Cher taken in 1985 at the White House. What an odd trio! Jenner is conservative and a Republican. He is also a Christian. When Diane Sawyer asked how he thought the conservative faction of his party would take to his news, he said he would be willing to meet with Republican leaders to discuss transgender issues. 06 of 33 Bruce Jenner in 1989 Photo by David Madison/Getty Images In this picture, Jenner is interviewed during the 1989 Bruce Jenner Bud Light Classic track meet held on May 27, 1989, at San Jose City College in San Jose, California. He looks much more feminine in this picture than in the shots of him in the 70s. He told Sawyer that he took female hormone drugs for five years in the 80s and had the hair on his face and chest removed via electrolysis. 07 of 33 Bruce Jenner in 1990 and 1991 with Wife Kris Jenner Getty Images -- Photo by Kypros/Getty Images and Photo by Donaldson Collection/Getty Images Jenner married Kris Kardashian on April 21, 1991, after five months of dating. Here are two shots of Jenner and Kris. The left photo is of them in 1990. They posed for the photo to the right in 1991. "Kris had the most difficult time of anyone in the family," said a Jenner insider to People magazine. "She has had a lot to process. She has cried a lot about this because it's an emotional thing for her." Jenner told Diane Sawyer that Kris took his news hard. ABC reported that of the three ex-wives, Kris would not comment on Jenner's transition. Kris later tweeted that she was watching the Diane Sawyer interview with Bruce next to her, so all was well. The day after the show aired, she tweeted, "Not only was I able to call him my husband for 25 years and father of my children, I am now able to call him my hero." 08 of 33 Bruce Jenner in 1991 with the Merged Kardashian-Jenner Families Photo by Maureen Donaldson/Michael Ochs Archives/Getty Images The Jenner-Kardashian families officially merged in 1991 when Bruce and Kris married. All of Jenner's children, both biological and step, have been supportive and his four oldest children appeared on the Sawyer special to publicly support their father. He told Sawyer that when he told them, “They all cried, mainly because they don’t want anybody to hurt Dad.” Bruce Jenner said that of all of his children and stepchildren with Kris Jenner, stepdaughter Kim had been the most open and accepting of his transition. Khloe, who he said had experienced a lot of loss in her life, had the hardest time. Kim Kardashian told "Entertainment Tonight" in January: "I think everyone goes through things in life, and I think that story and what Bruce is going through, I think he'll share whenever the time is right. "I guess I'll kind of let everyone be curious and I feel like that's his journey to talk about, I just think it's his story to talk about, not really mine." Pictured: (Middle row, L-R) Brody Jenner, Kourtney Kardashian, Bruce Jenner, Kris Jenner, Cassandra Jenner, Kim Kardashian (top row, L-R) Brandon Jenner, Burton Jenner (bottom row, L-R) Robert Kardashian Jr., Khloe Kardashian 09 of 33 Bruce Jenner in 2001 Photo by Alex Wong/Getty Images Jenner speaking during the 2001 Service to America Awards Presentation Ceremony in Washington, D.C. 10 of 33 Bruce Jenner on April 11, 2003 Photo by Frederick M. Brown/Getty Images Jenner and his family on April 11, 2003, in Hollywood, California. Jenner and Kris have two daughters together, Kylie and Kendall. 11 of 33 Bruce Jenner in August 2003 Photo by Rod Rolle/Getty Images Jenner at the 22nd Annual Santa Barbara Triathlon Aug. 23, 2003, in Santa Barbara, California. 12 of 33 Bruce Jenner in 2003 Photo by Tim Jackson/WireImage for Getty Images Bruce Jenner during the 2003 Celebrity Sports Invitational Ski Event in Squaw Valley at Resort at Squaw Creek in Lake Tahoe, California, United States. 13 of 33 Bruce Jenner in 2005 with Kris Jenner and Kourtney and Kim Kardashian Photo by SGranitz/WireImage for Getty Images Since late 2007, Jenner had starred with his wife, children and stepchildren in the E! reality series "Keeping Up with the Kardashians." Here, he's pictured with Kris Jenner, Kourtney, and Kim Kardashian during E! Entertainment Television's 2005 Summer Splash Event. “The one real true story in the family was the one I was hiding, and nobody knew about it,” he said to Sawyer. “The one thing that could really make a difference in people’s lives was right here in my soul, and I could not tell that story.” 14 of 33 Bruce Jenner in 2007 and 2009 Photo by John Shearer/WireImage and Photo by Jason LaVeris/FilmMagic) for Getty Images Here are two photos that show how much younger Jenner looked after his facelift. He started hormone drugs and got procedures to transition into a woman during these "Keeping Up With the Kardashian" years. He's pictured to the left on Nov. 5, 2007. The picture on the right was taken in July 2009. 15 of 33 Bruce Jenner in 2009 Photo by Jean Baptiste Lacroix/WireImage for Getty Images Bruce Jenner sighting on July 5, 2009, in Los Angeles, California. 16 of 33 Bruce Jenner in 2010 with Stepdaughter Kim Kardashian Jean Baptiste Lacroix for Getty Kim Kardashian and Bruce Jenner on April 7, 2010, in Los Angeles. Jenner told Diane Sawyer that Kim Kardashian's husband Kanye West helped her accept Jenner's situation. “Kim told me a story. She goes, ‘You know what really turned me around on thinking about this?’ I said, ‘What?’ She goes, ‘Kanye.’ I went, ‘Oh, okay,’” Jenner told Sawyer. “He says to Kim, ‘Look, I can be married to the most beautiful woman in the world, and I am. I can have the most beautiful little daughter in the world, and I have that. But I’m nothing if I can’t be me. If I can’t be true to myself, they don’t mean anything.’” Jenner then added, “Since then, Kimberly has been, by far, the most accepting, and the easiest to talk to about it.” 17 of 33 Bruce Jenner in September 2013 Photo by Laura Cavanaugh/Getty Images Bruce Jenner on Sept. 11, 2013, in New York City. 18 of 33 Bruce Jenner in November 2013 Getty Images Bruce Jenner on Nov. 11, 2013. 19 of 33 Bruce Jenner in January 2014 Splash News Will he do it? The rumors were ongoing that Jenner planned to undergo throat surgery to shave down his Adam's apple. This surgery is typically done on patients who are in the first stage of gender reassignment. At one point Jenner told TMZ that he hadn't decided whether he would undergo the surgery. He said he was doing it because "I just never liked my trachea." He had the surgery in January 2014. He told Sawyer that the media got wind of a doctor's appointment he had for his trachea and when he showed up, he saw the cameras. He immediately went home, paced his home realizing that his secret was indeed out. He thought about how easy it would be to kill himself, but decided that was not what he wanted. He wanted to live to see how this journey went. 20 of 33 Bruce in February 2014 Splash News Bruce began going out in ombre hair after his surgery. The tabloids went crazy. 21 of 33 Bruce Jenner With Kris Jenner in April 2014 Photo by GONZALO/Bauer-Griffin/GC Images for Getty Images Bruce Jenner and Kris Jenner show a united front at LAX on April 2, 2014, in Los Angeles, California. Jenner was married to Kris for 22 years before they announced their split in October of 2013. People reported a family insider as saying Kris Jenner is "looking back at their entire marriage. A lot of things are suddenly making sense." 22 of 33 Jenner on April 4, 2014 Photo by Ethan Miller/Getty Images for Getty Images Jenner on April 4, 2014 in Las Vegas, Nevada. 23 of 33 Bruce Jenner with Son Brody on May 5, 2014 Photo by Paul Archuleta/FilmMagic for Getty Images Brody Jenner and Bruce Jenner at the third annual Hank Baskett Classic Golf Tournament on May 5, 2014, in Palos Verdes Estates, California. Brody told Diane Sawyer that when his father told him his secret, it explained a lot of things. 24 of 33 Bruce and Kris in May 2014 for Kim's Wedding to Kanye West Photo by Neil P. Mockford/GC Images for Getty Images Kris Jenner and Bruce Jenner seen leaving the Four Seasons George V Hotel on May 22, 2014, in Paris, France. They were there for Kim's wedding to Kanye West. The couple announced their separation in October 2013, though they had actually separated a year earlier. Kris filed for divorce in September 2014 citing irreconcilable differences. Their divorce was finalized in December 2014, but became official on March 23, 2015, because of a six-month state legal requirement in California. 25 of 33 Bruce Jenner on Oct. 20, 2014 Photo by GONZALO/Bauer-Griffin/GC Images for Getty Images Kim Kardashian and Bruce Jenner seen on Oct. 20, 2014 in Los Angeles, California. 26 of 33 Bruce Jenner on Oct. 20, 2014 Getty Images From early on, the family was not fond of Bruce's growing hair, which he later wore in a ponytail. "I think we've ganged up on him as a group," Kris Jenner, who works as manager to many of her famous children, told the "Today" show. "Kendall and Kylie are on the pony patrol as we speak trying to get rid of it. I tried to manage it! I think it needs its own manager." After the divorce was filed, Jenner was free to wear his hair as he liked. 27 of 33 Bruce Jenner on his 65th Birthday, Oct. 28, 2014 X17 Online Bruce Jenner was pictured solo running errands near his home in Malibu on his birthday. Here he was pictured in his car and lighting up a cigarette, with his nails painted red. He told Diane Sawyer that now that he'd outed himself as a woman, he was looking forward to wearing nail polish long enough for it to chip. 28 of 33 In Touch Magazine's Disgusting Front Page Cover In Touch screenshot In Touch magazine hit a new low in their coverage of Bruce Jenner. They featured a PhotoShopped image of Jenner in red lipstick, his head placed on the body of a woman. The Kardashian family was so angry they reportedly cut off In Touch and Life & Style magazines from any interaction with them in the future. The powers that be at the influential civil rights group GLAAD were also not amused. “This nonsense has to end,” GLAAD president Sarah Kate Ellis said in a statement. “It’s long past time that media outlets stop gossiping about Bruce Jenner’s gender.” 29 of 33 And Finally, Landing the Coveted Cover Page of Vanity Fair Magazine Annie Leibovitz for Vanity Fair Here is Caitlyn's official coming out — in the July 2015 Vanity Fair cover story shot by Annie Leibowitz. 30 of 33 Caitlyn Jenner at the July 2015 Espy Awards Caitlyn Jenner at the Espy Awards, July 15, 2015. Getty Images: Kevin Winter This was Caitlyn Jenner's official coming out party to the public — when she took the stage in front of her entire family to accept an award at the 2015 Espys. 31 of 33 Caitlyn at a Culture Club Performance in Late July 2015 Caitlyn Jenner Attends Culture Club Performance, July 24, 2015. Kevin Winter for Getty Images Here she is, looking fantastic at a Culture Club performance on July 24, 2015. 32 of 33 Caitlyn Jenner at a Polo Classic Fundraiser on Sept 12, 2015 Caitlyn Jenner at a Polo Classic Fundraiser on Sept 12, 2015. Getty: Michael Bezjian Here's a picture of Caitlyn looking summery and casual in September. 33 of 33 Caitlyn on October 27, 2015 Getty: Tibrina Hobson and Gabriel Olsen Here, Cait attends a launch party. She celebrated her 66th birthday on Oct. 28 and on Oct. 29, Glamour Magazine named her one of their Women of the Year. The award honored Jenner for her determination to be "relentlessly open" and for "finding new meaning in her life."