The 66-year-old star of E!’s docu-series I Am Cait graced the red carpet in her blue, long sleeve silk gown with black lapel detail from Moschino Couture! by Jeremy Scott. She accessorized with Neil Lane diamonds and black pumps by Barollo Italy, reported People magazine.
Jenner didn’t run from the paparazzi, as she used to do before transitioning; she stood smiling as she posed with her trademark long tresses styled in a chic updo.
Backstage, she had her first encounter with supermodel Andreja Pejic and they exchanged numbers, according to Pejic’s publicist, who shared a photo of the two trans women standing with Jeremy Scott.
Accompanying Jenner was one of her daughters, Kylie Jenner, who posted on Instagram an explanation for her denim attire: “Had some major wardrobe malfunctions but that couldn’t stop me from supporting the ones I love. You’re amazing @caitlynjenner congrats on being woman of the year @glamourmag.”
Fellow Women of the Year awardees included actress Reese Witherspoon, dancer Misty Copeland, and designer Victoria Beckham. Last year, Laverne Cox became the first trans woman recognized by Glamour as one of the Women of the Year, in addition to being one of The Advocate's finalists for Person of the Year in 2014.
Actress Judith Light, one of the stars of Amazon’s Transparent, presented Jenner with her award after heralding the former Olympian for helping to “teach America what it means to live a courageous and authentic life.”
Jenner thanked Light for her steadfast support of the transgender community: “You have done so many things for so many gender-nonconforming people. Having you present this to me tonight means so much to me and our community."
"When it comes to gender, everyone in this room is on a journey," Jenner told the audience. "We are constantly learning and growing as human beings learning about ourselves, but there is a second part of this population when it comes to gender. There is massive confusion deep down inside."
She then shared a personal milestone she said she achieved just last week:
“I haven't been on the airlines for over a year. Why? Because I haven't had an authentic ID. Finally, last week I got my driver's license and gender marker F. It's always the little things in life. I am sitting on the plane for the first time reading Glamour magazine and not having to fold over the cover so no one can see what I was actually reading, and I had it opened up beautifully and just reading through Glamour magazine was absolutely great. So thank you, Glamour magazine for honoring me tonight. I never in a million years thought I'd be here and I am sure you didn't either."
Watch the clip of Light and Jenner from Glamour magazine below: