Jenner was raised with her sister and the Kardashians in Calabasas, an upscale suburb west of Los Angeles. Jenner attended Sierra Canyon School before switching to homeschooling in order to pursue modeling. She graduated in 2014. In May 2014, Jenner purchased a two-bedroom, 2.5-bath condominium in Los Angeles for US$1.4 million.
Jenner walked her first Society Management bookings for Marc Jacobs, Giles Deacon, Givenchy, Chanel, Donna Karan, Diane von Fürstenberg, Tommy Hilfiger, Fendi, Ports 1961, Bottega Veneta, Pucci, Dolce & Gabbana; Sonia Rykiel, and Balmain. Jenner participated in two Chanel public relations events in 2014: one, a feminist rally-themed Chanel event; and two, the company's Metiers D'Art in Salzburg. Jenner shot covers and editorials for Interview LOVE, and Teen Vogue. Jenner was cast in campaigns for Givenchy and a December-themed LOVE advent calendar promotion with Doug Inglish. In November 2014, Jenner became an official Estée Lauder representative. Jenner was hailed as "the 'It Girl' of the season" by LOVE editor Katie Grand.
Seventeen magazine featured Kendall and Kylie Jenner as Style Stars of 2011 and selected them as "Style Ambassadors" for the magazine. In 2014, the Jenner sisters co-authored novel Rebels: City of Indra with ghostwriter Maya Sloan. On May 24, 2016, the Regan Arts division of Phaidon Press announced that the Jenner sisters, Elizabeth Killmond-Roman, and Katherine Killmond created Time Of The Twins as a sequel to Rebels: City Of Indra. to be released November 15, 2016.
Jenner was named as one of People magazine's 50 most beautiful people in the world on April 9, 2014. Time magazine named the Jenner sisters as two of the 30 Most Influential Teens, once in 2014 and again in 2015. On December 16, 2014, Google named Jenner as the second most Googled model in the world. Jenner debuted at No. 2 on FHM's annual 100 Sexiest Women in the World list at the end of April 2015. Tumblr named Jenner as its most reblogged model for 2015. In November 2017, Forbes listed Jenner as the No.1 highest-paid model in the world.
Jenner joined Khloe Kardashian, Lil Twist, and The Game at PINZ bowling alley in Studio City, California, for a charity bowling game on January 19, 2014. The event was held to raise money for The Robin Hood Foundation, a nonprofit for which The Game pledged to raise US$1 million in donations. The Jenner sisters participated in singer Chris Brown's two Kick'n It For Charity Celebrity Kickball games in Glendale, California, on July 19, 2014 and on August 16, 2014. Jenner, Ansel Elgort, Gigi Hadid, and Jenner's agent Ashleah Gonzales encountered unhoused model/actor John Economou in Venice Beach during a fashion shoot on January 31, 2015, a meeting which led to Economou being signed to a Two Management contract by company president Luc Brinker. On February 14, 2015, Jenner appeared at Marc Jacobs' Bookmarc store in New York City for the launch of Love issue 13. She posed in a limited-edition T-shirt sale to raise proceeds for Designers Against AIDS.