Entertainment

Kendall Jenner’s Transformation and Best Looks Over the Years

We’ve seen Kendall Jenner grow up in front of our eyes — literally. The brunette beauty graced our TV screens on Keeping Up With Kardashians when she was just 11 years old and continues to do so today. Since her first days on the series, she’s branched out from her famous sisters and taken over the modeling world, making her quite the expert in fashion.

The TV personality has turned her passion into a super successful career. Kendall is currently the highest-paid model in the world, and she’s been No. 1 since 2017.

It turns out Kenny always knew she wanted to pursue a career in modeling. “I remember being 13 [or] 14 and making the funniest little book for my mom of photos of me that I took,” she divulged in a 2016 Vogue podcast. “I was like, ‘I want to be a model and you need to help me.’”

And of course, Kris Jenner helped her. Kendall’s vision was to become a Victoria’s Secret Angel someday, so her mom reached out to photographer Russell James a.k.a. “the guy who could really discover VS models,” according to the momager. Shortly after the two got in contact, Russell came to meet Kendall at her house.

“I said to Kendall, look, go upstairs and put on your cutest party dress,” Kris told Tommy Hilfiger at the WWD’s CEO Summit in 2017. “Brush your hair, put on your party shoes, and when he gets here, come downstairs.” Instead, the then-15-year-old opted for jeans, a top and platform shoes. Regardless of her casual outfit, though, she still managed to impress Russell. “He said, ‘You’re right, she’s beautiful, and I can’t wait to work with her,’” Kris added.

Eventually, Russell shot Kendall for his Victoria’s Secret-themed book called Angels, which was released in 2014. The following year, Kendall made her Victoria’s Secret runway debut. Then, in 2016, she walked with wings for the first time. Though Kendall never officially became a Victoria’s Secret Angel, she has left her mark on the world.

When she’s not behind the camera or strutting on the runway, the supermodel is spending time with boyfriend Devin Booker, with whom she sparked romance rumors in April 2020. The pair made their relationship Instagram official in February 2021 and have been “getting serious” ever since. “They make a really cute couple,” an insider told Life & Style exclusively. “She definitely sees a future together.”

Scroll through the gallery below to see photos of Kendall Jenner’s transformation and best looks over the years! 

Kendall Jenner Transformation Best Looks Through the Years

1998

Even before she turned 3 years old, Kendall was slaying the fashion game with her adorable bob. We guess we can thank mama Kris for that, considering she was her first stylist.

Kendall Jenner Transformation Best Looks Through the Years

2003

Remember when camouflage pants were the must-have trend? The then-7-year-old looked pretty in pink while her little sister Kylie Jenner rocked a bold green and orange outfit.

Kendall Jenner Transformation Best Looks Through the Years

2007

Kendall attended the 2007 Dash fall fashion show with her parents, and we’re not surprised that her outfit stood out so much. The blue really made her dark hair pop!

Kendall Jenner Transformation Best Looks Through the Years

2008

Hot pink is always the go-to for any pre-teen, and Kendall proved it. Her style couldn’t be more different than her big sister Kim Kardashian’s — even early on!

Kendall Jenner Transformation Best Looks Through the Years

2008

Long before Kenny rocked high heels, she was all about sneakers. We’re loving this girly punk-rock combo.

Kendall Jenner Transformation Best Looks Through the Years

2009

Kendall has never shied away from showing her teeth — even when she had braces. Many teens hate their smiles, but Kenny couldn’t help but always rock hers. We stan!

Kendall Jenner Transformation Best Looks Through the Years

2009

Kendall wasn’t a professional model yet, but she was getting some good practice with Kim. Also, peep the colorful nail polish — how cute!

Kendall Jenner Transformation Best Looks Through the Years

2009

For the 2009 ESPY awards, Kenny experimented with her look and began wearing shoes with a small heel. Who would’ve thought she would someday become a pro walking in them?

Kendall Jenner Transformation Best Looks Through the Years

2009

Not only do we love this little black dress, but we’re also so here for the confident pose she struck. Go, Kendall!

Kendall Jenner Transformation Best Looks Through the Years

2009

We see you, girl! The then-13-year-old looked fabulous in a black and white mini-dress paired with booties.

Kendall Jenner Transformation Best Looks Through the Years

2010

It’s rare to see such a casual look on the red carpet, but sometimes it works, and this was one of those times. We also can’t help but notice her braces-free teeth. Her smile is stunning!

Kendall Jenner Transformation Best Looks Through the Years

2011

At this point, then-14-year-old Kenny began looking a little more grown up as her style became more sophisticated. How chic is this ensemble, though?

Kendall Jenner Transformation Best Looks Through the Years

2012

Finally, the reality star embarked on her modeling journey. Clearly, she was made for the runway!

Kendall Jenner Transformation Best Looks Through the Years

2013

The following year, Kendall launched her PacSun clothing line with Kylie and her personal style shined through. Kendall and Kylie for the win!

Kendall Jenner Transformation Best Looks Through the Years

2014

Kendall shocked fans when she wore this gorgeous white bodysuit with black pants. It’s definitely one of her most iconic looks!

Kendall Jenner Transformation Best Looks Through the Years

2015

Obviously, red is her color. The hot shade makes the supermodel’s skin glow.

Kendall Jenner Transformation Best Looks Through the Years

2016

Kendall rocked a chic look for one of her Versace shows. At this point, she was taken far more seriously in the modeling industry compared to when she first started.

Kendall Jenner Transformation Best Looks Through the Years

2017

Only a year later and Kendall’s runway style looked more on the adult side. We’re so feeling this neutral-toned outfit!

Kendall Jenner Transformation Best Looks Through the Years

2018

For the Vanity Fair Oscars party, Kenny sported a black mini-dress that displayed lots of cleavage. Is there anything she can’t pull off?

Kendall Jenner Transformation Best Looks Through the Years

2019

For the Tiffany & Co. Flagship store launch, Kenny wore an over-sized baby pink dress. While this isn’t a look many can rock, she did it effortlessly.

Kendall Jenner

2020

Kendall looked like a doll walking the catwalk at Milan Fashion Week in February.

Kendall Jenner Accused of Photoshop Following Skims Campaign Selfie: 'Nobody Looks Like That'

2021

Kendall sent the internet into a frenzy after posing this revealing selfie for Kim Kardashian’s Valentine’s Day Skims campaign.

Kendall Jenner Met Gala 2021

2021

Kendall also stunned at the 2021 Met Gala on September 13 in New York City.

Source: https://www.lifeandstylemag.com/

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