For a foolproof sporty-chic moment à la Smalls, reach for an oversized rugby shirt and Comme des Garçon Converse sneakers. On chillier fall days, swap the shorts for a pair of jeans that will look just as cute. Vogue Club members were first to view this story: Join today to experience exclusive Vogue content before anyone else. Kendall Jenner was only 11 years old when Keeping Up with the Kardashians premiered in 2007. As a result, the 26-year-old model, who grew up on camera over the course of 20 seasons, has had her style moments rigorously documented. Jenner revisits some of those memorable outfits in a new “Life in Looks” video for Vogue. The 818 Tequila founder’s aesthetic has matured and refined in a remarkably short period of time: evolving from boho-chic at 2016’s Coachella Festival to original vintage Dolce & Gabbana worn at her eldest sister’s Italian wedding.
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.
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