When it came to unveiling her feminine style for the first time on the July cover of Vanity Fair, Caitlyn Jenner wanted to really look – and feel – the part.
“I mean these pictures – Annie [Leibovitz], Vanity Fair, spared nothing doing it right, and the wardrobe, everything involved with it were just, the people were just great,” Jenner said after the shoot. “It was, you know, two of the best days of my life.”
She described the final images as “over-the-top great,” despite being nervous about finding her authentic, female appearance.
“I was always worried – you never wanted to look like a guy in drag, you never wanted to look like a guy in a dress, okay. If you’re going to do that, come out, you really have to look the part,” Jenner explained.
She added, “You have to look very feminine, you have to be able to, what I call my presentation is extremely important because it puts people at ease. And if you can do that, okay, people are at ease, they’re just comfortable being around you.”
See The Life of Caitlyn Jenner
At the 1976 Summer Olympics in Montreal, Bruce Jenner won the gold medal in the decathlon, setting the world record at 8,616 points.Getty ImagesJenner became a national hero following his Olympic win and was later inducted into the Olympic Hall of Fame in 1986.Tony Duffy—Getty ImagesJenner became an NBC Sportscaster in the late 1970s following his Olympic performance in Montreal.NBC/Getty ImagesJenner married actress Linda Thompson, above, on Jan. 5, 1981, following his divorce with Chrystie Crownover.Getty ImagesJenner was diagnosed with dyslexia as a child. In October of 1985, he received the Outstanding Learning Disabled Achiever Award from then-First Lady Nancy Reagan alongside stars such as Cher and Tom Cruise.Getty ImagesJenner was a successful race car driver in the 1980s, though in a 2013 interview he said, "I was a lot more badass runner than I was a driver.”Ann Clifford—The LIFE Picture Collection/Getty ImagesIn 1991, Jenner married Kris Jenner, previously Kris Kardashian, just one month after she finalized her divorce from Robert Kardashian. The two had dated for only five months.Maureen Donaldson—Getty ImagesTheir marriage merged two already large families, evident here in this 1991 portrait.Donaldson Collection/Getty ImagesAfter his sports career, Jenner, seen here at a celebrity golf event in 1993, had a number of small acting jobs and television appearances.Stephen Dunn—Getty ImagesThe family poses at an event in 1995, the year Jenner and Kris welcomed the first of their two children together, Kendall Jenner.Ron Galella—WireImageKylie Jenner was born two years later in 1997. The girls can be seen here on the red carpet in 2000, long before they covered magazines and appeared on TIME's Most Influential Teens list.Scott Nelson—AFP/Getty ImagesJenner, seen here in 2005, would re-enter the spotlight thanks to Keeping Up With the Kardashians, which first premiered in 2007.Steve Granitz—WireImageJenner spoofed his reality-star fame with a commercial for Tropicana Juicy Rewards in 2010.APJenner and Kris, here at The Tonight Show with Jay Leno in 2011, announced their separation in 2013. She filed for divorce the following year.Kevin Winter—Getty ImagesJenner poses with a box of Wheaties in 2012. He appeared on the front of the box first in 1977 after his Olympic gold-medal win, then in 2012 when Wheaties rolled out a retro series.Noel Vasquez—Getty ImagesJenner appears with two of his sons, TV personality Brody Jenner and musician Brandon Jenner, who records with his wife as Brandon & Leah, at an April 2013 release party.Chelsea Lauren—WireImageJenner walks with step-daughter Kim Kardashian in October of 2014 — about five months after rapper Kanye West became his son-in-law.Bauer-Griffin—GC ImagesCaitlyn Jenner, formerly Bruce Jenner, appeared as a woman for the first time on the cover of Vanity Fair's June 2015 issue, photographed by Annie Leibovitz.Annie Leibovitz—Vanity FairCaitlyn Jenner accepts the Arthur Ashe Courage Award onstage during The 2015 ESPYS at Microsoft Theater on July 15, 2015 in Los Angeles.Kevin Winter—Getty Images
Now, the reality personality thinks that people might even wonder after seeing the portraits, “My God, why didn’t you do this earlier?”
The former Olympic gold medalist also talked about how she will celebrate her big reveal – by living her life.
“I’m going to go enjoy life. I have nothing left to hide. I am kind of a free person, a free soul,” Jenner explained to Bissinger.
“To be able to wake up in the morning, be yourself, get dressed, get ready to go out, and just be like a normal person. That’s a wonderful feeling to go through life,” Jenner said. “I’ve never been able to do that; it’s always been confusion, it’s always been, you know, I’ve got one side [with] boy clothes, the other side’s women’s clothes. It’s like I cleaned the whole closet out – the boys stuff is gone, okay?”
