See Photos of Penelope Disick and Her Famous Family as Kourtney Kardashian’s Eldest Daughter Turns 14

Penelope Disick is growing up fast.

The second Kardashian-Jenner grandchild — and Scott Disick and Kourtney Kardashian’s only daughter — turns 14 on July 8, 2026, but it seems like just yesterday that she made her big debut on the cover of Us Weekly. Over the years, Penelope has proven herself as one of the chicest members of the KarJenner clan with her colorful sense of style, and she often spends time with her parents, aunts, grandmother and cousins.

“Being her mommy is one of the greatest things I have ever done,” wrote Kourtney on Instagram for Penelope’s 13th birthday. “She inspires me to be a better person every day. I won’t ever have the words for how much joy and love she brings to my life. She is the cooooolessssst 🐞.”

From adorably matching her grandma Kris Jenner in lemon-printed dresses to seeing Beyoncé in concert with aunts Kim Kardashian and Khloé Kardashian and cousin North West, look back at some of the cutest — and coolest — moments from the first 14 years of her life.

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Tiny Tot

In celebration of her birthday in 2019, Grandma Kris shared a carousel of photos of her first-born granddaughter throughout the years, including this one of little “P” having fun with a balloon.

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Cousin Time

And of course, the Kardashian-Jenner family has grown many times over since Penelope was born in 2012.

In 2018, she spent some time with her baby cousin True Thompson, who was born earlier that year.

“My soul is complete because of you ❣️,” True’s mom Khloé wrote on Instagram alongside the photo of the cousins. “Please, Father Time, can you slow down just a little 🙏🏽 I love being an Auntie and a Mommy.”

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Mermaid Vibes

Penelope has been rocking some pretty epic costumes over the years, including his mermaid ensemble from a few years back. Since then, she’s dressed as a Cheetah Girl, Cher from Clueless and a character from Disney’s Princess and the Frog — group costumes she usually does with her cousin North West.

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Mommy’s Little Girl

As Kourtney’s first and only daughter, Penelope has always gotten lots of love from her mama.

Back in 2017, Kourtney wrote alongside this sweet photo, “‘You’ll be her first role model, her first friend, her first love.’ My little Poosh 💋”

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Making Lemonade

A pint-sized Penelope matched with her grandma in lemon-printed dresses. To make the little one’s ensemble all the more cute, she wore a matching headband, purse and even her tiny shoes had lemons printed across them.

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Golden Hour

Kourtney celebrated her baby girl’s 10th birthday with an Instagram post showing off her backyard bash in pajamas alongside loved ones.

“I feel so blessed to be the mommy of this little lady. She makes me so so proud every day and brings so much joy to my world,” she captioned the carousel, which included a glowing evening selfie of the mother-daughter duo. “Happy 10th Birthday my Penelope 💞🥳 filled with matching pajamas, fuzzy slippers, all sleeping together in blow up hearts, outdoor movies and lots of rainbow sprinkles.”

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Birthday Bash

In celebration of her 11th birthday in 2023, Kourtney brought Penelope on a sunny trip to Hawaii, which included spending some quality time with her little girl.

“Still beaming with joy from the l week I had taking 7 girls to Hawaii to celebrate my daughter’s birthday,” a then-pregnant Kourtney wrote alongside a carousel of photos from the getaway.

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Daddy & Me

Penelope also has fun with dad Scott, who documented their Labor Day weekend together back in 2022 that included a boat ride with Reign and cousin North West.

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All Dressed Up

And remember what we said about those costumes? “As if,” Kourtney wrote alongside the photo from Halloween 2021.

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Soaring, Flying

Seemingly aboard an airplane, Penelope flashes a peace sign alongside her dad in this photo from summer 2023.

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The More the Merrier

Penelope’s family has grown even more in recent years as her mom married Blink-182 drummer Travis Barker.

In this photo from Christmastime, the then-12-year-old is seen posing with her mom and Barker, brothers Mason and Reign, as well as Barker’s kids Landon and Atiana De La Hoya.

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Girls’ Night

Now, all grown up, Penelope has started attending big events with her family, which included Beyoncé’s Renaissance World Tour in 2023. Penelope matched in silver alongside her aunts Khloé, Kim and grandma Kris as well as North.

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Like Mother, Like Daughter

Both dressed in long coats, Penelope and her mom stopped for a mirror selfie.

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Beep, Beep

Penelope got behind the wheel of a golf cart and seemed to take her mom for a spin while wearing matching blue bucket hats.

Read the original article on People