The "I Am Cait" star stole the spotlight at Glamour's Women of the Year Awards in New York City on Monday, sporting a custom blue long-sleeved silk gown with a black lapel detail by Moschino Couture! by Jeremy Scott. She completed her elegant ensemble with Neil Lane diamonds, black pumps and a chic updo.
The 66-year-old star was joined by daughter Kylie Jenner at the star-studded soiree, but the 18-year-old had a wardrobe mishap that kept her from going full glam.
"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," she wrote on Instagram.
Cait was recognized as one of the mag's Women of the Year for her transgender advocacy work. Fellow honorees included Reese Witherspoon, Misty Copeland and Victoria Beckham.
Another style star to wow on the red carpet was Selena Gomez, who looked ravishing in a red Valentino patent leather mini that featured a sheer chiffon top and white collar. The "Good For You" singer accessorized her red hot look with metallic peep-toe pumps and a side-swept 'do.
Meanwhile, Witherspoon opted for floral frock by Erdem, which she paired with black platform sandals, dangling diamond earrings and a statement ring.
The ladies of "Orange Is the New Black" traded in their prison garb for glamorous gowns. Dascha Polanco and Uzo Aduba wowed in white, while Danielle Brooks showed off some serious cleavage in a three-toned, plunging blue dress.
Also in attendance at the Glamour gala were Serena Williams, Amy Schumer, Jared Leto, Karlie Kloss and many more. Check out all of the red carpet photos at the top!