The evolution of Kylie Jenner through every season of 'Keeping Up With the Kardashians'

June 2024 · 10 minute read
Updated

On season one, she shocked audiences by dancing on a stripper pole.

Kylie Jenner surprised viewers from the very first episode of "KUWTK." E!

The two youngest Jenner sisters seemed to live a pretty normal life during the first season of the show.

Kylie wanted to have fun with Kendall, and in one episode, they filmed Kylie playing with her parents' stripper pole while their half-brother, Brody Jenner, was babysitting.

Kris and Caitlyn weren't happy with Brody for recording her mini "Girls Gone Wild" skit. They also irritated Caitlyn when Kris let the girls bring home a puppy, Bella.

Kylie started growing up during season two.

Khloé Kardashian with Kylie Jenner during season two. E!

The family's burgeoning fame didn't seem to greatly impact the youngest members so Kylie led a fairly normal tween life on season two.

In one episode, Khloé attempted to teach her little sisters about puberty. Though Kylie was eager to discuss her bodily changes, Kendall was shy about it all.

Season three captured the early stages of Kylie's love of makeup.

Kylie Jenner even debuted a streak in her hair. E!

As family members took on the roles of well-known celebrities, they became busier, appearing in magazines and ad campaigns and traveling the world.

Kylie was on the cusp of becoming a teenager and began experimenting with makeup, much to the chagrin of her parents.

Kylie and Kendall were also concerned when they overheard their parents discussing Caitlyn's colonoscopy, thinking that their parent might be ill. Caitlyn was nervous to explain it, but the girls were relieved to learn it's a simple procedure that many adults go through.

Kylie faced tension with some of her siblings on season four.

Kylie Jenner was hurt by her sisters. E!

On the fourth season of "KUWTK," Kendall expressed interest in modeling, which seemed to upset Kylie, who felt her older sister was being given special attention due to her budding career prospects.

Kylie and Kendall were also both upset with Kim when she lied about spending time with them by pretending she had a foot injury and needed to rest. However, Kim eventually apologized for being dishonest.

Kylie was worried about her parents and their marriage on season five.

Kylie Jenner on season five. E!

By the show's fifth season, the camera caught tension between Kris and Caitlyn, which made Kylie and Kendall worried about their parent's arguments.

Kylie and Kendall were afraid that they were headed for divorce, but Kris and Caitlyn reassured them that they were just going through a rough patch.

Kylie was also upset upon learning that Kris was hiding a secret smoking habit, and she plotted with Kendall and Kourtney to get her to stop smoking.

On the sixth season, Kylie and her mom faced some tension.

Kylie Jenner soon embraced her inner teen. E!

Now that both Jenner girls were in their teenage years, they wanted to hang out with their friends without parental supervision.

Kris had a hard time dealing with her youngest daughters' growing independence and tried to insert herself in their ice-skating and jump-rope sessions. The girls explained that although they love spending time with their mom, they also wanted to spend time with friends.

Tensions rose further when they went behind Kris's back to enlist Scott Disick's help. Kris was furious that Disick was meddling in their personal and professional lives.

Season seven saw Kylie start to come into her own.

Kylie Jenner started to get busier on season seven. E!

The young Jenners started exploring new opportunities, like becoming West Coast contributors to Seventeen magazine.

Kylie was easily able to approach strangers on the street as part of the job, though Kendall was more reserved. Their increasingly busy schedules led them to miss school, and Kylie noted that being far behind gave her anxiety.

Kris then began to consider homeschooling her daughters. Both girls also nearly ruined a white carpet with red sauce and tried to hide the evidence from Kris on season seven.

Kylie faced more growing pains during season eight.

On season eight, Kylie Jenner turned 16. E!

Kylie turned 16 on season eight and became much more independent.

When she said felt like she needed some space from Kendall and to spend time with friends separately, Kendall was hurt, and Khloé, Kim, and Kourtney stepped in to help them work out their differences.

Kylie also showed off her burgeoning fashion sense, which Kim tried to emulate.

She also had an "Alice in Wonderland"-themed Sweet 16, though Kris wanted her to have a more childish soirée. Still, Kris trusted Kylie's artistic vision and the party was a success.

Season nine featured a lot of changes.

On season nine, Kylie Jenner had colorful hair. E!

The ninth season of "KUWTK" brought plenty of ups and downs, as Caitlyn and Kris announced they were separating. Though each family member was concerned about Kendall and Kylie's reactions, they seemed to understand that it was for the best.

The family also took a trip to Thailand, and Kylie and Kendall became frustrated with the family's bickering. When they disappeared one day, they panicked the rest of the crew but were later found safe after escaping for a massage and some shopping in the local town.

The youngest sisters also published their first book, "Rebels: City of Indra," a young adult sci-fi novel during this season.

Kylie's signature lips first appeared on season 10.

Kylie Jenner soon started her empire. E!

Season 10 saw Kylie begin to focus on her own projects. Though she was still worked on her clothing lines with Kendall, she also started her first solo venture, a line of hair extensions.

She also purchased her first home but the chief storyline surrounding Kylie was her lips as she was unsure of how to handle newfound media attention surrounding her appearance.

Kylie admitted that she was always insecure about her lips, which then become her most famous feature as she promoted her Kylie Lip Kits.

Her family also seemed worried when Kylie began spending more time alone, even on group trips.

She graduated high school and turned 18 on season 11.

On season 11, Kylie Jenner had a blonde moment. E!

Season 11 was a milestone year for Kylie, as she graduated high school, celebrated her 18th birthday, and got a new Ferrari. Kris threw the girls a joint graduation party and met Caitlyn, who came out on an earlier season, for the first time at Kylie's birthday party.

Kylie also became more serious with longtime boyfriend Tyga, which frustrated Kendall, who felt she was not as close to her sister as she once was.

Kendall was angry when Kylie brought Tyga on an "all-girls" trip to St. Barts, but Kylie reminded her family that they've all brought significant others on trips before.

Fame started to wear on Kylie by the 12th season.

Kylie Jenner got tired of paparazzi. E!

By season 12, Kylie and the rest of her family were so famous, paparazzi and fans would approach them even if they were just running errands.

Kylie, Kendall, and Khloé decided to mess with their followers by dressing up in wacky costumes — complete with wigs and prosthetics — to enjoy a "non-famous" day out touring Hollywood.

Kylie discussed the anxiety she experiences from being so famous, especially after the launch of her Lip Kits were successful. Kylie said she wasn't sure she actually wanted to be famous, telling Kim, "Some people are born for this life and others aren't and I just know I'm not."

Kim empathized with her and shared that Kanye helped her to care less about what people say and think.

Kylie stepped away from the spotlight during season 13.

Kylie Jenner was noticeably absent from the opening of her pop-up store and season 13. E!

Fans didn't see much of the youngest Jenner sister during season 13, with speculation largely leading to the fact that she'd gotten her own spin-off, "Life of Kylie," at that time and her then-reported pregnancy.

Kylie's absence continued in season 14 until she said she was pregnant in the finale.

Kylie Jenner made a small appearance. Facebook/Keeping Up With The Kardashians

After remaining absent from the show during season 14, Kylie reemerged in the finale when fans got to see her baby bump.

Pregnancy worries were front and center during the first part of season 15.

Kylie Jenner stayed out of this season for a few episodes. E!

Kylie didn't make an appearance until the fourth episode of the season when Khloé told her she was hesitant to announce her first pregnancy for fear of overshadowing Kylie's entrance into motherhood.

But Kylie assured her sister that she doesn't actually want to tell the world she's expecting, telling Khloé, "I don't want to be in the spotlight. I just want to be low-key." Kylie didn't announce her pregnancy until after she'd given birth to her daughter, Stormi.

During season 16, viewers saw Kylie reacting to a lot of friend-related drama.

Kylie Jenner spoke quite a bit on this season. E!

Season 16 focused on the family's reactions to Tristan Thompson's cheating scandal involving Jordyn Woods, Kylie's (now former) best friend.

Following the cheating reports, Kylie said she was "scared" of Woods.

"I'm in a very weird position because I care so much about my family," Kylie said during one episode this season. "I also care about Jordyn. Right now I feel like it's a lot of ups and downs — sad, angry. It's a roller coaster of emotions, and I don't know, I just don't know what to say."

Kylie wasn't on season 17 that much.

Kylie Jenner seemingly stepped back from the show a bit. E!

Kylie didn't appear much on this season, as she was likely busy with her business and her daughter.

A few episodes mentioned the drama with Woods, and Kylie spoke about how she felt the whole situation was necessary because Woods had been her "security blanket." 

On the season-17 finale, Kylie didn't attend a family trip to Wyoming, which left some of her sisters and her mom quite upset. She later apologized, saying she was bringing her daughter, Stormi, to visit her dad, Travis Scott, and she hadn't realized how important the trip really was.

Season 18 featured Kylie working on some big collaborations and getting surgery.

On season 18, Kylie Jenner got LASIK. E!

On season 18, Kylie got LASIK eye surgery after receiving encouragement from her friend, Stassie Karanikolaou.

She also spoke about celebrating her 22nd birthday on a yacht trip and preparing for a Paris Fashion Week collaboration with Balmain.

On season 19, Kylie got into some drama with Kendall.

Kylie Jenner got into an argument with her sister on season 19. E!

On season 19, Kris planned a trip to Palm Springs in an effort to get her daughters to put aside their difference, but a fight between Kendall and Kylie ruined plans for a getaway.

However, Kylie apologized to Kendall and the two got along smoothly for the rest of the season.

Kylie and the rest of her family celebrated the series finale on season 20.

Kylie Jenner reflected on the legacy of her makeup brand in the final season of "Keeping Up With the Kardashians." E!

On the final season of "Keeping Up With the Kardashians," Kylie and her sisters reflected on how their lives have changed since the TV show first aired.

The show also captured some behind-the-scenes footage of Cardi B's "WAP" music video, in which Kylie appeared.

On the series finale, Kylie contributed the first three lip kits she launched to the family's time capsule, saying, "there is no Kylie without Kylie lip kit."

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