In 2007, Jenner, along with her parents and siblings, Kylie, Kourtney, Kim, Khloé, and Rob, began appearing in the reality television series Keeping Up with the Kardashians, which chronicles the personal and professional lives of their family members. The series was successful for its network, E!, and has resulted in the creation of numerous spin-offs including Kourtney and Kim Take Miami, Khloé & Lamar, Kourtney and Kim Take New York, and Kourtney and Khloé Take The Hamptons, in which Jenner has made multiple guest appearances.

Jenner began her reality television career in 2007 as a supporting actor in her blended family’s E! program Keeping Up with the Kardashians and its subsequent related spinoffs Kourtney and Khloé Take Miami, Kourtney and Kim Take New York, and Khloé & Lamar.

Jenner began modeling at age 13 when Wilhelmina Models signed her on July 12, 2009. Cinematographer Nick Saglimbeni directed the photoshoot for Jenner’s Wilhelmina portfolio. Jenner’s first modeling job was the Rocker Babes with a Twist campaign for Forever 21 in December 2009 and January 2010. Jenner featured in a Teen Vogue Snapshot on April 19, 2010.

In 2010, Jenner was cast in boy band One Call’s Blacklight video along with Ashley Benson and Kevin McHale. In 2012, Jenner appeared as AJ on the Hawaii Five-0 episode “I Ka Wa Mamua”. Jenner did voiceover for the character Strawberry in The High Fructose Adventures of Annoying Orange episode “Shakesparagus Speare”, which aired on January 20, 2014. In August 2014, Jenner appeared in singer PartyNextDoor’s video “Recognize” with sister Kylie Jenner and rapper Drake. Jenner made a cameo appearance in the heist film Ocean’s 8, which was released on June 8, 2018.

In September 2011, Jenner walked for Sherri Hill during Mercedes-Benz Fashion Week. By the end of 2012, Jenner had covers on American Cheerleader, Teen Prom, Looks, Raine, GenLux, Lovecat, and Flavour Magazine. and booked campaigns for White Sands Australia, Leah Madden, and Agua Bendita. In November 2012, Jenner teamed with Victoria’s Secret photographer Russell James for editorial work and joint projects. Over the course of 2013 and 2014, their work together surfaced in Kurv, Miss Vogue Australia, and Harper’s Bazaar Arabia. Jenner featured in James’ Nomad Two Worlds: Australia book launches in Sydney and Los Angeles. Jenner’s editorial work signaled a change of direction to high fashion, and Jenner signed with The Society Management on November 21, 2013.

Jenner created two signature nail lacquers for the 2011 Nicole by OPI Kardashian Kolors nail polish line, for which the Jenner sisters eventually earned a combined US$100,000 in endorsement profit. On March 16, 2012, the Jenner sisters were named Creative Directors of the Gillette Venus Gets Ready with Kendall & Kylie Jenner webisode series, which was originally aired on Gillette’s Facebook page. In July 2013, the Jenner sisters formed a partnership with Pascal Mouawad’s Glamhouse to create the Metal Haven by Kendall & Kylie jewelry collection. In February 2014, the Jenner sisters launched a shoe and handbag line under Steve Madden’s Madden Girl line for Nordstrom.

The Jenner sisters previewed The Kendall & Kylie Collection with PacSun on November 15, 2012; the collection launched in February 2013. On February 3, 2015, the Jenner sisters confirmed Kendall + Kylie collaboration with Topshop, which they unveiled in November 2015 at the Chadstone Shopping Centre in Melbourne, Australia. The collection launched in New York on February 8, 2016. On April 27, 2016, the Jenner sisters previewed a summer swimwear collection.

Jenner set up an eBay account where she auctions old clothing to raise money for Children’s Hospital Los Angeles. The Kardashian and Jenner sisters used eBay in this way to raise money for their charities in 2013. Jenner joined her family in a charity yard sale on November 10, 2013. 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.

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.

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. Jenner took part in publicity campaigns for Balmain x H&M and walked in the 2015 Victoria’s Secret Fashion Show. Jenner shot covers and editorials with Marie Claire Indonesia, Harper’s Bazaar, GQ, Vogue China, LOVE, and Vogue issues in Japan, France and America. Jenner featured in campaigns for Marc Jacobs, Karl Lagerfeld, Fendi, Balmain, Estée Lauder, a political campaign for Rock The Vote/Independent Journal Review voter registration, and a second LOVE advent calendar. Jenner signed contracts with Calvin Klein Jeans in March and Penshoppe in May.

In September 2015, each of the Jenner and Kardashian sisters released paid subscription mobile app websites in collaboration with Whalerock Industries. Jenner’s website was nominated for an International Academy of Digital Arts and Sciences 2016 Webby Award in April of that year. The Jenner sisters partnered with Glu Mobile to develop an app spinoff of Kim Kardashian: Hollywood; the Kendall and Kylie app launched February 17, 2016.

Beginning 2015, Jenner featured in a series of commercial ads for various products including Jenner’s signature Pure Color Envy Matte Sculpting Lipstick. Jenner has also promoted various other non-signature products from the product line throughout the year. In February 2016, Jenner and beauty blogger Irene Kim became guest editors for the Estée Edit, accompanied by a signature Eyeshadow Palette.

Jenner’s rapid career ascent led Dazed magazine’s editors to rank her top creative to watch out for in 2015 on their annual Dazed 100 list, Jenner collaborated with the editors on a Mean Girls-inspired “Burn Book” parody, which responded to her online critics and industry detractors. The video was later shortlisted on September 22, 2015, for the International Academy of Digital Arts and Sciences’ annual Lovie Awards in the Internet Viral Video category.

In 2016, Jenner and Cara Delevingne were recreated as wax figures for Madame Tussaud’s London Fashion Week Experience event. Jenner walked for Chanel, Diane Von Fürstenberg, Vera Wang, Michael Kors, Marc Jacobs, Fendi, Versace, Bottega Veneta, Balmain, Dior, Elie Saab, and Miu Miu. Jenner shot covers and editorials in Vogue Brazil, W Korea, LOVE, Vanity Fair, V, Self Service Magazine, and Harper’s Bazaar. Vogue’s editors devoted a special edition editorial supplement to Jenner in April.. Jenner had campaign features for Mango, CPS Chaps, Calvin Klein, Rock The Vote/Independent Journal Review, and Denimlab. Jenner announced her signing to Chilean retail chain París in April.

In 2016, Jenner began a career as a photographer, her first published work was photographing and styling Kaia Gerber, daughter of supermodel Cindy Crawford, for the sixteenth anniversary issue of LOVE.

On February 10, 2016, lawyers representing Jenner Inc. filed a $10 million lawsuit against esthetic medical company Cutera at the United States District Court for the Central District of California. Jenner’s legal team objected to the company using her brand without authorization. Cutera had featured Jenner in ad campaigns for its Laser Genesis acne treatment. In May 2016, Jenner’s attorneys dropped the charges.

The rapid ascension of the Instagirls has accelerated a decade-long reassessment of the interaction between fashion and mass consumption. Jenner’s adeptness at connecting with Millennials online has given her access to a large demographic market, with the ability to segment her fanbase and find ideal clients. Designer Sally LaPorte claimed Jenner’s approval of her line helped the designer key into the particulars of her ideal buyers. Former Calvin Klein Women’s Creative Director Francisco Costa praised Jenner’s social cachet: “Her social media reach is just incredible […] As a house, you become part of the culture by embracing someone like her.” Jenner’s ongoing participation in Calvin Klein promotions have proven to be profitable, as parent company the Phillips-Van Heusen Corporation announced a 13% increase in Net Sales over the previous year’s 1st quarter on May 26, 2016, with the financials also indicating a 10.5% increase in Revenue As Reported over the previous year’s quarter, and a 20.1% increase in Constant Currency Earnings before Interest and Taxes over the previous year’s quarter. According to CEO Emanuel Chirico, increased earnings reflect restructuring of the company’s global creative strategy for Calvin Klein and its associated #MyCalvins ad campaigns.

Jenner’s 2017 campaign for La Perla caused some controversy when she had to cancel a previously scheduled appearance as a Victoria’s Secret model due to her new affiliation with La Perla.

In 2017, Kendall Jenner was paid $275,000 for an Instagram post announcing that some members of the G.O.O.D Music family would be performing at Fyre Festival, and that her followers could buy tickets using a discount code she provided. The post, which has since been deleted, was not tagged as an #ad despite Jenner’s compensation and the Federal Trade Commission law which requires paid posts on social media to be disclosed transparently. Fyre Festival was a fraudulent “luxury music festival” founded by Billy McFarland, CEO of Fyre Media Inc, and rapper Ja Rule. 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. Jenner said, “You get reached out to by people to, whether it be to promote or help or whatever, and you never know how these things are going to turn out, sometimes it’s a risk, I definitely do as much research as I can, but sometimes there isn’t much research you can do because it’s a starting brand and you kind of have to have faith in it and hope it will work out the way people say it will. You never really know what’s going to happen.”

Jenner was at the center of public scrutiny in April 2017 after starring in a commercial for Pepsi called “Live for Now”. The commercial cast her in a role in which she used the beverage to make peace between police officers and protesters. This ad was criticized for borrowing imagery from the Black Lives Matter movement and trivializing the protests against police brutality, particularly as it affects African Americans. Pepsi pulled the ad within a day, and apologized to Jenner for “putting [her] in this position.” She was reportedly “devastated” by the ad, although she “had the right to approve the ad before it was released”. According to the same source, Jenner’s contract with Pepsi prohibited her from commenting on the fallout.

In June 2017, Kendall and her sister, Kylie, launched a line of “vintage” T-shirts on their website for their lifestyle brand, Kendall + Kylie. 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.) with bright images or logos associated with the Jenners superimposed over them. The shirts were met with criticism from the public, as well as several cease and desist letters from the estates of the musicians and artists that were featured without permission. The photographer whose portrait of Tupac Shakur was used has since sued the Jenner sisters for copyright infringement. The sisters pulled the shirts from their website and issued a joint apology, “to anyone that has been upset and/or offended, especially to the families of the artists.” 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. It was reported that Global Brands Group (GBG) previously listed the Kendall + Kylie brand on its website. 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”

She started dating NBA player Blake Griffin in summer 2017. The two broke up in April 2018. In June 2018, Jenner began her relationship with baskeball player Ben Simmons. The couple split in May 2019.

On her birthday in 2017, Jenner launched a birthday campaign and invited fans to donate $22 in honor of her turning 22 to Charity: Water, a non-profit organization bringing clean and safe drinking water to people in developing countries. Jenner with her brand Zaza World launched merchandise that benefit Coronavirus relief efforts, and one hundred percent of the net profits went to Feeding America, the nationwide network of food banks which supports shelters, soup kitchens, and underserved communities.

In a 2018 interview with Love magazine, Jenner made a statement, which was posted to the magazine’s Instagram account, about not walking in a large number of shows during fashion week, which is typical for a working high fashion model.

In 2019, Jenner faced another controversy after her mother, Kris Jenner, announced that Kendall was going to be sharing “her most raw story in order to make a positive impact for so many people and help foster a positive dialogue.” The announcement was revealed to be a partnership with the skin-care company Proactiv. It was deemed as an insensitive and misleading publicity stunt, especially after it was revealed that she uses her family dermatologist, Christie Kidd, and was widely criticized on Twitter. In January 2020, she confirmed that a cosmetics line in collaboration with her sister Kylie’ Kylie Cosmetics was in the process. Kylie Cosmetics launched Kendall Jenner x Kylie Cosmetics on June 26, 2020.

Jenner has partnered with Moon, an oral-care brand created by Shaun Neff of Neff Headwear. Jenner helped create one product for the brand, the Kendall Jenner Teeth Whitening Pen in April 2019. In October 2020, she launched a stain-removal toothpaste in collaboration with Moon and designer Heron Preston on a limited edition orange stain-removal toothpaste, with just 350 units available on online marketplace StockX. This collaboration simultaneously marking StockX’s debut into the personal care/beauty realm.

In November 2020, Jenner faced large public criticism after having a birthday party with a hundred plus attendance during the coronavirus pandemic. The party was attended by many celebrities, including Justin and Hailey Bieber, The Weeknd, and Winnie Harlow, despite Los Angeles county having a Safer-at-Home order in affect. 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. So, you know, we do what we can, we, we try to follow the rules.”