Caitlyn Jenner has worn many hats throughout her life — and has always looked fantastic doing so.
Jenner (born Bruce Jenner) was introduced to the world in 1970 when she began her career as a decathlete during the Drake Relays in Iowa, where she was a physical education major at Graceland University and had previously played college football. She went on to compete in the 1972 and 1976 Summer Olympics, winning a gold medal in the latter’s decathlon event in Montreal. She decided to retire from the sport soon after.
“In 1972, I made the decision that I would go four years and totally dedicate myself to what I was doing, and then I would move on after it was over with,” the Olympian said at the time. “I went into that competition knowing that would be the last time I would ever do this.”
After winning gold, Jenner became a legend in her own right, appearing on the covers of Sports Illustrated, GQ and Playgirl in addition to becoming a spokesperson for Wheaties. The photogenic athlete also became a star in Hollywood, with roles in the 1980 movie Can’t Stop the Music and the NBC crime drama CHiPs in 1981. She even landed her own video game, Bruce Jenner’s World Class Decathlon, in 1996.
Jenner made the move to reality TV in 2007 when she and then-wife Kris Jenner invited E! viewers into their home and documented the lives of their blended family on Keeping Up With the Kardashians. Caitlyn and Kris married in April 1991 and welcomed two daughters together: Kendall Jenner and Kylie Jenner. The momager also shared Kourtney Kardashian, Kim Kardashian, Khloé Kardashian and Rob Kardashian with her late ex-husband, Robert Kardashian, while Caitlyn had Burt Jenner and Casey Marino with first wife Chrystie Crownover as well as Brandon Jenner and Brody Jenner with second wife Linda Thompson.
“I am so fortunate. I have the best home movies in life,” the athlete said on her YouTube channel in 2020 after the Kardashians announced the end of their reality series. “I’ve watched all my kids grow up on the network, go through everything that they’ve gone through over the years — from marriages to divorces to kids now being born to watching Kendall and Kylie grow up.”
After Caitlyn and Kris divorced in 2015, the New York native came out as a transgender woman in a 20/20 interview with Diane Sawyer and on the cover of Vanity Fair. She has since been a vocal advocate for trans rights.
Scroll down to see a timeline of Caitlyn through the years.

Caitlyn's high school yearbook photo from senior year showed the future Olympian with feathered brown locks and a fuller face.
Seth Poppel/Yearbook Library
Gold medal! Caitlyn set a record in the 1976 Summer Olympics in Montreal for her performance in the decathlon.
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Caitlyn posed for a portrait in Sports Illustrated looking au naturel and, dare we say it, ruggedly handsome.
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Caitlyn and Thompson were all smiles at an event in Los Angeles.
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Caitlyn was spotted at a tennis match with her first wife, Crownover.
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Sporting longer locks and a bright red bow tie, Caitlyn attended the 10th annual Women's Tennis Association Dinner at the Plaza Hotel in New York City.
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Baby on board! A pregnant Kris (expecting daughter Kendall at the time) looked happy on a grinning Caitlyn's arm at the Batman Forever premiere in Los Angeles.
Ron Galella, Ltd./WireImage.com
Time flies! Five years later, the couple proudly posed with Kendall and Kylie at the premiere of The Emperor's New Groove in Hollywood.
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Family affair! While attending E!'s Summer Splash Event, the star posed with Kris and stepdaughters Kourtney and Kim.
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Bodyguard! Caitlyn walked around Manhattan with stepdaughter Kim on her arm.
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Caitlyn grinned next to stepdaughter Khloé at her 2009 wedding to NBA player Lamar Odom. (Khloé and Odom split in 2013.)
Jake Holly/Startraksphoto.com
Caitlyn returned to her classic look from the '80s with shorter hair on the Extra set in Los Angeles.
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Caitlyn rocked a visor and athletic apparel on the golf course at the George Lopez Celebrity Golf Classic.
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Following a procedure to soften the appearance of her Adam's apple, Caitlyn had to be helped into her car in Los Angeles. "I just never liked my trachea," she told TMZ.
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With ombre locks, Caitlyn stepped out to film Keeping Up With the Kardashians in L.A. An insider told Us at the time that Caitlyn has "never felt comfortable in [her] own skin."
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Caitlyn stepped out in L.A. after the new year and let her ever-growing long locks flow free. During a season 9 episode of KUWTK, she snapped at Kris while getting highlights done by celeb stylist Tracy Cunningham. “You’re not allowed in here!” she barked.
Coleman-Rayner
The golf lover showed off a larger pout while filming I Am Cait with Khloé in Pismo Beach, California. A source told Us she was not nervous about sharing her journey on TV. “She feels like she has nothing to lose,” the insider said. “She wants to live this way before it is too late."
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Caitlyn was involved in a multiple-vehicle accident on the Pacific Coast Highway in Malibu that killed activist and actress Kim Howe. Prosecutors later declined to file criminal charges against the reality star, whose SUV ran into Howe’s car.
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Caitlyn captivated the world in April 2015 when she sat down with Sawyer for an emotional 20/20 interview. She came forward with the truth about her gender identity, telling the journalist, "I am a woman."

The reality star reintroduced herself as Caitlyn with the stunning July 2015 cover of Vanity Fair. "If I was lying on my deathbed and I had kept this secret and never ever did anything about it, I would be lying there saying, ‘You just blew your entire life,'" she told the magazine. "'You never dealt with yourself,' and I don't want that to happen."
Annie Leibovitz/Vanity Fair
For her first big public appearance after her transition, Caitlyn wowed in a formfitting white Versace gown — which she later said was inspired by a similar gown Angelina Jolie wore to a movie premiere in 2010 — to accept the Arthur Ashe Courage Award at the 2015 ESPYS in L.A. The former athlete teared up as several members of the Kardashian-Jenner clan cheered her on from the audience.
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Caitlyn conquered her fear of wearing a women’s bathing suit in public and rocked a white one-piece during an episode of I Am Cait. “Putting on a bathing suit represents a lot to me,” she said. “It did feel very freeing.”
Courtesy of E!
Caitlyn copied Duchess Kate's navy blue Issa London wrap dress (which Kate wore to her engagement announcement to Prince William in 2010) when the reality personality stepped out in L.A. and showed she’s truly fashion-forward.
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Another gorgeous gown! Caitlyn wore a custom blue Moschino gown when she was honored as the Transgender Champion at Glamour’s Women of the Year Awards in NYC. “Glamour magazine Woman of the Year and Olympian decathlon gold medalist,” she told Sports Illustrated in June 2016. “This has got to be the greatest double of all time, right? It will never be matched.”
Jamie McCarthy/Getty Images for Glamour
Caitlyn, along with many of the Kardashian-Jenner family member, attended Kanye West’s Yeezy Season 3 launch during New York Fashion Week — and she even matched with daughter Kendall in a similar distressed cream Balmain for Yeezy sweater dress.
Kevin Mazur/Getty Images for Yeezy Season 3
The celebrated Olympian participated in a golf tournament at the Ladies Professional Golf Association’s ANA Inspiration Pro-Am.
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Caitlyn donned a black Chiara Boni gown for the 2016 Time 100 Gala in New York City, where she was recognized as one of the magazine’s 100 most influential people.
Kevin Mazur/Getty Images for Time
A big year! Caitlyn celebrated her “first birthday” by posing with her Vanity Fair cover. “Can’t believe it’s been one year since the @vanityfair cover. So happy, best year of my life #happyfirstbirthday #callmecait #learningtolive,” she wrote on Instagram.
Courtesy Jenner/Instagram
E! canceled I Am Cait, which won a GLAAD Media Award for Outstanding Reality Program, after two seasons.
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Caitlyn confirmed during another interview with Sawyer that she had undergone gender reassignment surgery, saying, “I wasn’t less a woman the day before I had the surgery than the day after the surgery, because that did not define who I am as a human being.”
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The Olympian pulled back the curtain on her childhood, career, marriages and transition in her memoir, The Secrets of My Life. A source exclusively told Us at the time that the Kardashian-Jenners were “upset” about the book and “tired of being caught off guard.”

After graduating from Pepperdine University in Malibu, Sophia Hutchins moved in with Caitlyn, sparking rumors that the transgender activists were a couple, which they have long denied. “I date guys. And Caitlyn’s like, ‘I gotta sign off on him,’” Hutchins, who is also the star’s manager, said on the “Juicy Scoop” podcast in May 2020.
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Caitlyn competed on season 19 of I’m a Celebrity…Get Me Out of Here! in the U.K. After finishing in sixth place, she did not have any family members waiting to greet her as contestants typically do. She later told the Daily Mail that she “texted or called all the kids to apologize” for the backlash they received over the snub.
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Caitlyn and Hutchins attended the 2020 Vanity Fair Oscar party, where they met up with Kim.
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