Relive Kendall Jenner's Top Moments From the Decade: From Teen Reality Star to Top Model

By Kelsey Klemme Dec 29, 2019 2:00 PMTags
Watch: Kendall Jenner Dishes on New Show With Kirby Jenner

Sometimes, it seems like just yesterday that Kendall Jenner was a shy teenager on Keeping Up with the Kardashians.

At least, that was the case a decade ago, when the show was only in its fourth season. Now, ten years later, Kendall has grown up in front of our eyes into a successful model and businesswoman who has also had a lot along the way.

The 24-year-old is one of the most sought after faces to walk down the runway of high-end designers like Tom Ford and Balmain, with the star also landing campaigns like being the face of Stuart Weitzman's 2019 fall collection.

The celebrity has also become a producer as she is developing a show for the new content platform Quibi that is scheduled to launch in 2020.

We've also seen her steal the spotlight with viral moments like impersonating her sister Kylie Jenner or setting the Internet ablaze when she and her sisters dressed as Victoria's Secret angels for Halloween in 2018.

Of course, it wasn't too much of a costume for Kendall—the model had a dream come true in 2015 when she got selected to walk on the stage of the Victoria's Secret Fashion Show, an honor she got to repeat two more times, too.

Kendall Jenner Impersonates Kylie in the Best Way

Of course, some moments of the past decade have been anything short of fun.

Kendall unfortunately had multiple incidents of a man trespassing on her property and got caught up in the whole Fyre Festival drama as an influencer.

However, she has her solid family by her side to get through it all.

Take a look back at Kendall's most memorable moments of the decade below!

Kendall's Empire

Kendall Jenner was only 14 years old at the start of the decade, and while she watched her older sisters build their empires, she started the foundation for hers, too.

True fans remember that in 2010, there was an episode of Keeping Up with the Kardashians where Kris Jenner sets Kendall up at Wilhelmina Models and she got to work with designer Sherri Hill, kicking off the start of her now iconic modeling career.

In the past ten years, Kendall has walked for many legendary fashion houses, like Burberry, Fendi, Versace, Balmian and Tom Ford, to name just a few. One of the model's biggest achievements was making the cut to walk at the Victoria's Secret Fashion Show, debuting on the brand's infamous program in 2015. 

Kendall will also be producing a show for Quibi alongside Kirby Jenner, the performance artist who has consistently been curating an Instagram where he Photoshops himself into the model's pictures.

Kendall's Viral Moments

While Kendall's high-fashion looks from the runway frequently go viral, the Los Angeles native has also been a trending topic for being her funny, authentic self.

Earlier this year, Kendall was caught at a hockey game impressively chugging a beer and giving Game of Thrones actress Sophie Turner a run for her money on which star is best at downing the beverage.

Also, the model made us laugh when she impersonated her makeup mogul sisterKylie Jenner, by purposely overlining her lipstick and getting it all over her teeth on a recent episode of Keeping Up with the Kardashians.

Kendall's Style

Kendall's off-duty style is just as fierce as it is on the runway!

Around town running errands, the 24-year-old rocks athleisure looks that have us emptying our bank accounts to recreate.

However, where her style evolution truly shines is on the red carpet or at iconic events, such as the Met Gala.

Kendall rocked this year's Met pink carpet with a feathery Donatella Versace gown that made the star look like a rising phoenix and was fire.

She also took the amfAR Gala at Cannes by storm in a pink Giambattista Valli tulle dress that later showed up in the brand's collaboration with H&M.

The 5'10" trendsetter can pull off any bold outfit or element, like her gown at this year's Emmys that featured a latex turtleneck component.

Kendall's Relationships

Over the past ten years, the reality star's love life has included flirty, rumored flings like Blake Griffin and Jordan Clarkson and alleged relationships we'll never forget, like being romantically linked to A$AP Rocky and Harry Styles

Kendall and the former One Direction singer famously dated on and off for a few years, including getting caught packing the PDA on a yacht in 2016.

The two still have a great friendship and even recently appeared on The Late Late Show with James Corden together, playing the show's game "Spill Your Guts or Fill Your Guts," where Styles ate cod sperm rather than answering what songs of his were about his ex.

Kendall now seems to be reconnecting with Ben Simmons, who she had dated in 2018. We're staying tuned to see how this relationship blossoms into the next decade!


While Kendall's past ten years were full of fun, there were also times that were downright terrifying for the star.

Back in 2018, Kendall got a five-year restraining order against a man who repeatedly trespassed on her property.

Also, Kendall found herself wrapped up in controversy after promoting the Fyre Festival experience on her Instagram, an event that went down as a disaster and was famously broadcast in real-time on social media.

The celeb has found herself the subject of a lawsuit from the event's trustee, Gregory Messer, to try to reclaim some of the funds from the event that the star promoted.

Kendall's Family

Kendall is now the sole sister without kids, which is a big change from the start of the decade when the only baby in the Kardashian family was Kourtney Kardashian's son, Mason.

However, Kendall loves to joke that now that with "so many new babies," she may be the favorite aunt!

Kendall's Transformation

Finally, the model has transformed over the past decade with her style and beauty regimen, growing up in front of our eyes from the quiet teen she was into the trendsetting fashionista she has become.

Kendall's career on the runway has translated to her everyday style, where she rocks edgy looks that we totally covet.

She also has experimented with her hair, from a brief stint as a blonde to getting bangs. 

Whatever the next decade has in store for Kendall, we can't wait to watch!