After working in commercial print ad campaigns and photoshoots, she had breakout seasons in 2014 and 2015, walking the runways for high-fashion designers during the New York, Milan, and Paris fashion weeks.

Jenner has appeared in campaigns, editorials, and cover shoots for LOVE and various international Vogue editions, and is a brand ambassador for Estée Lauder.

The series debuted on October 14, 2007 and revolved around Jenner, along with her parents Kris and Bruce (now Caitlyn) and siblings, Kylie, Kourtney, Kim, Khloé, and Rob.

[18] The series was successful for its network, E!, and has resulted in the creation of spin-offs, including Kourtney and Kim Take Miami (2009), in which Jenner has made guest appearances.

[64][65] 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.

[70] In 2015, Jenner walked for Chanel, Alexander Wang, Diane von Fürstenberg, Donna Karan, Vera Wang, Michael Kors, Marc Jacobs, Oscar de la Renta, Giles Deacon, Fendi, N°21, H&M, Balmain, the annual Dosso Dossi Fashion Show in Antalya, Turkey, Givenchy, Elie Saab, and Ports 1961.

[78] In 2016, Jenner and Cara Delevingne were recreated as wax figures for Madame Tussaud's London Fashion Week Experience event.

Jenner shot covers and editorials in Vogue Brazil, W Korea, LOVE, Vanity Fair, V, Self Service Magazine, and Harper's Bazaar.

In July 2013, the Jenner sisters formed a partnership with Pascal Mouawad's Glamhouse[100][101] to create the Metal Haven by Kendall & Kylie jewelry collection.

On February 3, 2015, the Jenner sisters confirmed Kendall + Kylie collaboration with Topshop,[105] which they unveiled in November 2015 at the Chadstone Shopping Centre in Melbourne, Australia.

[109][110] In September 2015, each of the Jenner and Kardashian sisters released paid subscription mobile app websites in collaboration with Whalerock Industries.

The shirts retailed at $125 and featured logos or images of famous musicians or bands (Tupac Shakur, The Doors, Metallica, Pink Floyd, and The Notorious B.I.G.)

In June 2020, the Jenners sisters addressed reports that their fashion brand Kendall + Kylie has failed to pay factory workers in Bangladesh as a result of the coronavirus pandemic.

As a result, the Jenners stated that their company is owned by a separate entity known as 3072541 Canada Inc. even though they say that their brand "has worked with CAA-GBG in the past, in a sales and business development capacity only" and that they "do not currently have any relationship at all with GBG".

In February 2016, Jenner and beauty blogger Irene Kim became guest editors for the Estée Edit,[128] accompanied by a signature Eyeshadow Palette.

[132] Jenner did voiceover for the character Strawberry in The High Fructose Adventures of Annoying Orange episode "Shakesparagus Speare", which aired on January 20, 2014.

[138] 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.

[145] The party was attended by many celebrities, including Justin and Hailey Bieber, the Weeknd, and Winnie Harlow, despite Los Angeles County having a stay-at-home order in effect.

[146][147] Jenner's mother responded to the criticism, telling Andy Cohen, "we are really responsible, and we make sure that everyone in our family and our closest friends are tested religiously.

[162] Jenner's adeptness at connecting with Millennials online has given her access to a large demographic market, with the ability to further segment her fan base and find ideal clients.

[165] According to CEO Emanuel Chirico, increased earnings resulted from the restructuring of the company's global creative strategy for Calvin Klein and its associated #MyCalvins ad campaigns.

The app's deployment worked to Jenner's advantage; she ranked as D'Marie's #1 fashion influencer across all categories as of February 19, 2016,[171] with the ability to earn between US$125,000 and US$300,000 for a single update to her social media platforms.

Three months after Netflix and Hulu released incriminating documentaries revealing the corrupt and unorganized preparations behind Fyre Festival, Jenner apologized for her involvement during an interview with the New York Times.

[181] In April 2017, Pepsi cast Jenner as the star for the commercial advertisement in a role in which she used the beverage to make peace between police officers and protesters.

[185] On June 28, 2017, the Jenner sisters announced that they would be releasing a line of vintage T-shirts for their Kendall + Kylie line of clothing called Rock vs. Rap,[186][187] featuring the likenesses of various rock and rap artists[188] including The Notorious B.I.G., Tupac Shakur, Metallica, Pink Floyd, The Doors, Ozzy Osbourne, and Led Zeppelin, with pictures of the Jenner sisters superimposed over them.

[186] The announcement of this line of products was met with swift backlash from relatives and representatives of the figures depicted on the shirts themselves, including Sharon Osbourne,[189] Jeff Jampol,[190] and Voletta Wallace, mother of Biggie Smalls.

[202] Proceeds from the sale were donation-matched and sent to Share Our Strength: No Kid Hungry and the Greater Los Angeles Fisher House Foundation.

Jenner and Kim Kardashian attended a Christmas Eve visit with the kids at Children's Hospital Los Angeles on Tuesday December 24, 2013.

[204] Jenner, with her sister, Kylie, participated in singer Chris Brown's two Kick'n It For Charity celebrity kickball games in Glendale, California, in 2014[205] and on August 16, 2014.

[209] In 2020, Jenner, with her brand, Zaza World, launched merchandise to benefit Coronavirus relief efforts; net profits went to Feeding America, a nationwide network of food banks which supports shelters, soup kitchens, and underserved communities.