Skip to main content

Rare Pics Of Kendall Jenner You Probably Haven’t Seen

min read

By ActiveBeat Author

Kendall Jenner has grown up in the public eye. She has spent most of her life being followed by photographers while out and about, and even had her entire childhood documented on a hit reality show. We have watched her go from being an awkward tween to a show-stopping supermodel. Despite all this attention, there are still some moments in time that have flown under the radar.

We’ve rounded up some older pics that most people aren’t familiar with. Check out these rare pics of Kendall you probably haven’t seen:

25. Ristorante Puny – 2022

On May 20, 2022 Kendall Jenner and Devin Booker were photographed walking hand in hand — a rare sight! The two were headed out for dinner at Ristorante Puny in Portofino, Italy. They were later joined by the rest of the Kardashian family as they were all in town for Kendall’s sister, Kourtney Kardashian’s wedding to Travis Barker.

NINO/GC Images

24. Staples Center – 2021

A celebratory kiss! Another rare showcase of affection between these two love birds. Devin Booker ran over to the sidelines to hug and kiss Kendall Jenner after his team, the Phoenix Suns’ won against the L.A. Lakers at the Los Angeles Staples Center on October 22, 2021.

According to the press, Kendall had been cheering him on court-side throughout the game and right after the buzzer, he made a beeline toward the supermodel. He also handed out some high fives to some nearby spectators.

Kevork Djansezian/Getty Images

23. Soho New York – 2021

As a supportive girlfriend, Kendall Jenner flew to New York City to watch her boyfriend, Devin Booker play basketball. Before heading out for a date on Saturday night, they were seen walking through Soho in New York City before grabbing lunch at Bar Pitti.

Gotham/GC Images

22. Los Angeles, California – 2022

Keeping it casual! The supermodel and professional basketball player were spotted walking around West Hollywood in Los Angeles on May 24, 2022. They were both dressed casually and actually quite matchy-matchy as they both paired a grey top with dark pants. This photograph was taken after their whirlwind trip to Italy to celebrate a family wedding.

MEGA/GC Images

21. Abbey of San Fruttuoso – 2022

Kendall Jenner and Devin Booker were once again photographed while in Italy for Kourtney Kardashian and Travis Barker’s wedding. They were captured on their way to another meal together, this time for lunch at the Abbey of San Fruttuoso on May 21, 2022. The two seemed to coordinate outfits as they both dressed head to toe in beige.

NINO/GC Images

20. KIIS-FM’s Wango Tango – 2009

In 2009, Kendall attended 102.7 KIIS-FM’s Wango Tango with her sister Kylie and her mom, Kris. She did have braces at this point and looks absolutely adorable with her aqua dress and her boots. She was still clearly figuring out her style.

Noel Vasquez/Getty Images

19. Easy A Premiere – 2010

The budding model went for a really girly look at the L.A. premiere of Easy A. Her modeling career was starting to take off at this point. She had just landed a new gig in Lucca Couture‘s latest ad campaign.

Tinseltown /

18. Marc Jabos Runway – 2014

Jenner didn’t really look like herself when she walked the Marc Jacobs runway during Mercedes-Benz Fashion Week in 2014. She rocked this short, gold dress while rocking these blunt bangs that really hid her face. /

17. Abbey Dawn Fashion Show – 2011

The tall brunette joined her sisters Kourtney, Kim, and Kylie for the Abbey Dawn Spring 2012 fashion show at the Metropolitan Pavilion. She showed off her figure in this silky, white dress, which she paired with black wedges.

Ray Tamarra/Getty Images

16. Rob Dyrdek Foundation’s ‘Sk8 For Life’ Benefit – 2010

Kendall showed up at the SK8 4 Life event benefiting the Rob Dyrdek Foundation in 2010 with her sister Kylie. It must have been a good time. Travis Barker, The Cool Kids, and Rob Dydrek and Friends, as well as N.E.R.D performed.

Noel Vasquez/Getty Images

15. Premiere of The Vow – 2012

In 2012, the Forever 21 model attended the premiere of The Vow, which starred Rachel McAdams and Channing Tatum. She wore this white cocktail dress with a pair of bronze pumps, which made her look super slender and tall.

Tinseltown /

14. Sherri Hill Spring 2012 Collection – 2011

Jenner was never your average teenager. Here she is at the age of 15 getting ready to walk the runway for Sherri Hill. She’s got multiple people working on her hair as they try and get the young reality TV star runway ready.

© Jennifer Graylock/

13. Variety Power of Youth Event –2010

The Keeping Up with the Kardashians star arrived at the Variety Power of Youth event in 2010 in a simple yet stylish ensemble. She rocked a white top with a short black skirt and a pair of black and gold Steve Madden flats.

Kathy Hutchins /

12. Fashion’s Night Out Celebration – 2012

The TV personality rocked a stylish gold minidress by Azzedine Alaia with a pair of bronze-colored pumps to Fashion’s Night Out Celebration. She was there with her younger sister Kylie, who was dressed in sequined pants by Cameo and a tank top by Phanuel.

Emiley Schweich/Everett Collection

11. Kendall’s Garden – 2009

It turns out that Kendall has a bit of a green thumb! Here she is in 2009 at the family’s Calabasas home planting a vegetable garden with her mom and sisters and her brother Rob. She didn’t look too excited about being photographed, but at least she was going to have fresh produce!

Kristian Dowling/KK/Getty Images for GI

10. Sherri Hill Spring 2012 Collection Runway – 2011

Although Kendall wasn’t initially excited about the possibility of becoming a runway model, she quickly changed her mind. In 2011, she walked the runway for Sherri Hill’s spring 2012 collection in this jeweled prom dress.

lev radin /

9. 19th Annual “Race To Erase MS” – 2012

The budding model appeared at the 19th Annual “Race To Erase MS” event in Los Angeles in 2012. She went for a simple beige dress with metallic stripes and a pair of Mary Jane pumps while she posed with her sister Kylie on the red carpet.

© Jill Johnson/

8. Teen Choice Awards – 2011

The teen star attended the Teen Choice Awards in 2011 with her sister Kylie and her half-sisters Kourtney, Kim, and Khloe. Kendall was the real stand out on the red carpet. She wore this purple Aurelio Costarella dress with a Ted Rossi ring, a Kotur clutch and YSL heels.

© Jill Johnson/

7. Onitsuka Tiger’s Record Release Party for Selena Gomez & The Scene – 2009

Several years back, Kendall and her sister Kylie were good friends with Selena Gomez. In 2009, Kendall attended the Onitsuka Tiger’s record release party for Gomez and her band, The Scene. She attended the event with her sister Kylie and posed inside with Gomez.

Toby Canham/Getty Images

6. The Grove – 2011

When the Keeping Up with the Kardashians star was a teenager, she was a cheerleader for Sierra Canyon High school. That’s the school she attended until she switched to homeschooling. In 2011, she posed in her cheerleading outfit at The Grove during a visit with Extra.

Noel Vasquez/Getty Images for Extra

5. The Grand Opening of Kardashian Khaos – 2011

Kendall joined her sisters for the grand opening of the Kardashian Khaos store at The Mirage Hotel in Las Vegas. The aspiring model went for a super simple look with this navy blue cocktail dress and nude pumps.

© Arlene Richie/

4. Photoshoot with Kim – 2009

Over the years, the Kardashian-Jenner family has had many pets. Here Kendall is with her older half-sister Kim and two of their dogs, Dolce and Bella, during a photo shoot in Los Angeles in 2009. During the shoot, they also posed in the pool and on a motorbike.

Michael Caulfield/KK/Getty Images for GI

3. 8th Annual Teen Vogue Young Hollywood Party – 2010

Jenner was just an up and coming teen star when she attended the 8th Annual Teen Vogue Young Hollywood Party in 2010. She went for a cute outfit that consisted of a green mini-skirt, a white blouse with a black bow tie and a pair of simple sneakers.

Featureflash Photo Agency /

2. Espy Awards – 2009

Kendall joined her father at the 2009 Espy Awards. She rocked this white dress, which featured numerous ruffles, and a pair of silver strappy heels. She looks so young in this picture! She would have been just 13 years old!

©Jill Johnson/

1. Sherri Hill Spring 2012 Collection Runway – 2011

The aspiring model looked like a complete natural during her runway debut in the Sherri Hill fashion show in 2011. This white, feathery number looked amazing on her. She was clearly the biggest star of the show!

lev radin /

ActiveBeat Author