"Had some major wardrobe malfunctions but that couldn't stop me from supporting the ones I love," she wrote on Instagram.
"You're amazing @caitlynjenner congrats on being woman of the year for @glamourmag."
We've known lesser women cancel a night out over a broken heel, but Kylie proved that even among a sea of glittering dresses a simple black cropped top and trouser combo topped with an oversized vintage denim jacket can make the right style statement if worn with pride.
Kylie gave Caitlyn a big hug after she received the award for Transgender Hero at Glamour magazine's 25th Awards to honour iconic women's endeavours in various fields.
Have a scroll through the the rest of the red carpet looks and find full details of the award winners in the gallery below: