Kylie Jenner has been in the spotlight most of her life. The world watched as she navigated her teen years and transitioned into a successful businesswoman and mother: All with a dedicated tribe of family and friends standing by her side. Throughout the years, Jenner has kept a close circle, though not every one of her famous friendships has stood the test of time. the timeline of Kylie Jenner's friendships show just how loyal of a group the makeup mogul keeps.
Jenner has made headlines for her famous friendships, but she's also remained a dedicated pal to some of her childhood BFFs. Those friendships have turned into roommates, employees, and a full-on support system for Jenner and her daughter, Stormi. At any given time, Jenner can be found vacationing with her crew, hanging out with them around Los Angeles, and even doing joint YouTube videos where it's all just fun and games.
Jenner may be one of the most famous women in the world, but it's her friends and family who really make her who she is. But the friends Jenner keeps close (and the ones she has let go) also say a lot about the business mogul.
Karanikolaou and Jenner have grown increasingly close on social media since 2018, but according to Jenner, Stassi has been a staple in her friend group from the very beginning.
“You’ve been the most consistent and loyal friend in my life,” Kylie told Stassi during a Teen Vogue interview in April 2015. "I feel like without you, I wouldn’t be the person I am today. Because I wouldn’t be weird anymore. I’d be trying to be normal.”
In 2020, Karanikolaou and Jenner are closer than ever and the model is frequently seen appearing on Jenner's Instagram feed or making guest appearances in her hilarious TikTok videos.
Jenner and Woods were practically inseparable during their late teen years and early 20s. They even filmed a reality show together in 2017. However, that all changed in February 2019 when Woods and Khloe Kardashian's then-boyfriend Tristan Thompson were caught kissing at a party in Los Angeles.
The situation seemed to be too much for Jenner to forgive and forget. “I think that this whole Jordyn situation needed to happen," Jenner told Kardashian during an episode of KUWTK while the two reflected on the situation. "For me, for you, for her, for everybody. She was my security blanket. She lived with me. We did everything together. It just felt like, 'Oh, I have Jordyn, I don’t need anything else,' and I feel like there’s a part of me that needed to grow without her.”
Since Jenner's KUWTK comments, she hasn't spoken out about her once-close friendship with Woods.
Jenner and Richie were both thrust into the spotlight at a young age because of their respective famous families, including Richie's dad, iconic musician Lionel Richie. The pals were first photographed together at an event in 2014, and ever since, have been on hand to celebrate each other's biggest life moments. But their worlds really collided in 2017 when Richie started dating Jenner's sister Kourtney's ex Scott Disick.
The friends didn't let things get awkward between them, though, and continued to be there for each other in the years that followed. In August 2019, Richie even referred to Jenner as her "best friend."
“Kylie, you’re 22 and you’ve always been one year cooler than me,” Richie said in a birthday tribute video. “But I love you. You’re my best friend. I don’t know what life would be like without you.”
While Jenner and Richie don't seem to hang out in 2020 as much as they used to, even after Richie and Disick split, they didn't have a public fall out either. They could have just grown apart.
Jenner and Smith go way back. The duo even dated as teenagers in 2013, but split shortly after news of their romance was confirmed by Us Weekly. Luckily, their relationship wasn't strained, and the two remain close friends today.
In 2020, Smith and Jenner are the type of friends who can count on each other to be there to celebrate their life's biggest moments, and often run in the same circles of friends.
Jenner met Villarroel in 2012 after she applied for a job with Jenner Communications, and the rest is history. “They hired me as an office manager,” Villarroel told Insider in January 2020, adding that it just so happened Jenner was in need of an assistant. “I was already on payroll, and the girls already knew me so it was just easy to have me do it."
While Villarroel was employed as Jenner's assistant, they were closer than most friends. Even after Villarroel quit in 2019, the pals remain on good terms. Villarroel addressed speculation there was beef between the two in an Instagram Story in January 2020.
“I worked with Kylie for 5 years and she became one of my closest friends," Villarroel wrote. "We both decided it was time to grow without each other professionally about a year ago! she’s still one of my best friends and our relationship has only gotten stronger. now let’s focus our time and energy on other things! a lot is happening in the world right now.”
These days, it's unclear if the pair is as close as they were when Victoria worked for Jenner, but she still appears in Jenner's IG stories like in January when they stepped out for glamorous night together.
Jenner and Palmer first bonded around 2013 over their love of beauty products. “About six years ago, I started doing her lashes, and her whole family, they’re just very, very sweet,” Palmer said during a May 2020 interview with In The Know. “Slowly but surely we started building a relationship, and over every year it’s just gotten stronger and stronger.”