In June 2017, Jenner was placed at number 59 on the Forbes Celebrity 100, which calculates the 100 highest-paid celebrities of the previous 12 months, after earning approximately US$41,000,000, making her the youngest person on the list at 19 years old. Jenner collaborated with Melbourne-based sunglasses brand Quay Australia to release a line of sunglasses, Quay x Kylie.
Jenner starred in a reality show revolving around her life, Life of Kylie, which premiered in August 2017. On mother's day 2018, Kylie Cosmetics launched makeup line called Kris Cosmetics, in collaboration with her mother Kris Jenner. Jenner and her half-sister Kim Kardashian launched their second collaboration KKW x Kylie Cosmetics collection on Black Friday 2018 after previously launched the first collection in 2017.
In April 2017, Jenner and Tyga broke up mainly because of their distinguishable age difference. Jenner states that their breakup didn't end badly nor with a big fight. Rather it was the fact she was so young and she didn't want to look back and regret how she spent her life as a young woman. The same month, Jenner and Travis Scott met at Coachella where he was performing for part of his tour. They were seen hitting it off the entire night at the event and Kylie ended up going on the rest of the tour with Travis which kicked off the start of their relationship. A month later Jenner was spotted in pictures with Travis at the Met Gala and reported to be exclusive.
In 2017, Woods appears on Jenner's reality TV show, Life of Kylie, which showed how they maintained their friendship with their personal lives.
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, featuring the likenesses of various rock and rap artists 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. 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, Jim Jampol, and Voletta Wallace, mother of Biggie Smalls. They were also criticized on social media and were called "insensitive." Wallace, The Doors' manager and the estate of Jim Morrison issued a cease-and-desist letter to the Jenner sisters, writing that they did not authorize the sisters' use of the likenesses of these musical icons. The Jenners apologized for the shirts, and pulled them from retail.
In February 2017, Australian singer Kylie Minogue won a legal battle against Jenner for name trademark "Kylie". Jenner had filed a U.S. trademark application for use of the name "Kylie" for "advertising services" and "endorsement services" in 2015.
In January 2017, make-up artist Vlada Haggarty claimed that Jenner had stolen the creative style and aesthetic of her own work, such as the dripping gloss lip and golden finger tips, for her own products, and that Jenner had a history of taking Haggerty's original dripping lip art and passing it off as her own. Jenner later credited Vlada on social media and her work on the creation of the logo and an undisclosed settlement was paid to avoid any future legal issues.