The first look in Jenner’s trip down memory lane was what she wore to the season one premiere party for Keeping Up. “I remember these dresses so well,” Jenner says of the cheetah-print and blush-pink dresses she and Kylie wore, respectively. “Kylie and I always had matching clothes,” she says. “My mom and Kourtney had a children’s clothing store called Smooch. I’m pretty positive both of these dresses were from Smooch.” Next up, Jenner revisits walking for Marc Jacobs for the first time in 2014. She recalls wearing a sheer top for the New York designer—and, surprisingly, not feeling unnerved by the prospect of strutting down a runway with hundreds of eyes trained on her. “I was totally game,” she says of the pivotal moment, which she prepared for by taking some “walking lessons” at her agency’s offices. Only a year later Jenner would make her first appearance in the pages of Vogue, working with renowned creative director Grace Coddington and photographers Mert & Marcus on an Alice in Wonderland-inspired shoot. Kendall dived headfirst into the experience: donning a blonde wig for the first time and a disco-glam Miu Miu dress. “This was one of the first times I felt like modeling was working for me and was taking off,” Jenner says.
There have been some, in Jenner’s opinion, style missteps from time to time. (But seriously, let those who haven’t erred in their sartorial choices cast the first stone). Jenner cringes when she lands on a 2016 image of herself at Coachella, rocking a festival-ready flowing maxi dress and Yoko One-inspired sunglasses. “This was the vibe at the time,” Jenner says, laughing. “You need to understand! Would I wear this now to Coachella or anywhere? I don’t think so.” The star delivers rich behind-the-scenes details while revisiting her Met Gala looks. One standout was the custom Off-White look she wore in 2018, designed by the late Virgil Abloh. Jenner has fond memories of the beloved designer, saying, “Most of our conversations were over FaceTime. But you never felt like there was a disconnect. He always was putting all of his energy into it. So you always felt really comfortable and safe in his arms, in a way.” Another great Gala tidbit: Jenner’s 2019 outfit, which was designed by Versace and coordinated with Kylie’s own Versace number, featured pieces made the night before. “My stylist at the time went in and just drew the feathers out and said, “Versace can you do this overnight?” Jenner says, sharing her amazement at the skill and speed of the Versace team.
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