Honestly, if you look at a photo of the Jenner sisters from 2007, it’s basically unrecognizable. We’re talking about the pre-filler, pre-runway, and definitely pre-billion-dollar-valuation era. It’s wild to think that when Keeping Up With the Kardashians first aired, Kendall was just a 12-year-old moody tween and Kylie was only 10. They were just... kids. They were literally running around their Calabasas house, fighting over the TV remote and begging Kris Jenner for a dog.
People love to talk about the "glow up," but they usually skip the awkward middle parts. Kendall and Kylie younger years weren't just about being in the background of Kim’s drama. They were actually building a blueprint for modern fame before they even had high school diplomas.
The "Moody Tween" Era (2007–2010)
Back in the early seasons of the show, they were the "little sisters." Period. Kylie was often seen as the more outgoing, rambunctious one—remember her on that stripper pole in the first episode? Kendall, on the other hand, was the shy, lanky girl who seemed almost uncomfortable in front of the cameras.
Their fashion back then? Total chaos. Think mixed zebra prints, bright neon colors, and those weirdly specific coordinating outfits Kris used to put them in for red carpets. It was the peak 2000s SoCal aesthetic: denim cut-offs, Ugg boots, and lots of Justice-style accessories. Honestly, they probably look back at those photos and cringe just as much as we do at our own middle school pictures.
But while they were just kids to the viewers, the industry was already watching. By 13, Kendall had signed with Wilhelmina Models. Her first big gig wasn't some high-fashion couture show; it was a "Rocker Babes with a Twist" campaign for Forever 21. It’s kinda crazy to think her massive career started with a fast-fashion ad in 2009.
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When Things Actually Started Shifting
Around 2011 and 2012, the vibe changed. They weren't just "the kids" anymore. Seventeen magazine named them "Style Ambassadors," and they started hosting movie premieres like The Vow and The Hunger Games. This was the era of the PacSun collaboration—the quintessential Cali-girl brand. If you were a teenager in 2012, you probably owned at least one romper or high-waisted short from their collection.
Key Milestones from the Younger Years:
- 2011: 16-year-old Kendall walks her first runway for Sherri Hill.
- 2012: The sisters officially launch their PacSun clothing line.
- 2014: Kendall has her high-fashion "breakthrough" walking for Marc Jacobs, Givenchy, and Chanel.
- 2015: Kylie launches the first three Lip Kits (Candy K, Dolce K, and True Brown K).
Wait, we have to talk about the Lip Kits.
Before the $1.2 billion valuation and the Coty deal, there was just a 17-year-old girl with a major insecurity about her lips. Kylie's "over-drawn" lip phase in 2014 sparked a literal global conversation. People were obsessed. When she finally admitted to fillers in 2015, she didn't just hide; she capitalized. She took $250,000 of her own modeling money and turned it into an empire. That first launch of 15,000 kits sold out in seconds.
The Sibling Dynamic Nobody Talks About
A lot of people assume there was this cutthroat competition between them. Like, who’s the prettiest? Who’s more successful? But Kendall has been pretty vocal lately about how that just wasn't the case. In a 2024 interview with Vogue, she basically said they never competed over looks or fame. They fought over the remote. That was it.
They were "stuck as a duo" for years, but by the time they hit their late teens, their paths diverged in a big way. Kendall became the "clean girl" prototype—sleek buns, minimal makeup, and high-fashion runways. Kylie became the "King Kylie" of Snapchat—blue hair, heavy glam, and a social media presence that could literally move stock prices.
They even wrote a dystopian sci-fi novel together in 2014 called Rebels: City of Indra. Yeah, seriously. It’s one of those weird pieces of pop culture history that everyone seems to have collectively forgotten. Did they actually write every word? Probably not, but it shows how much they were trying to find an identity outside of just being "Kardashian adjacent."
Life "At-Home" vs. The Public Eye
While most kids were going to prom, the Jenner sisters were being homeschooled to keep up with their careers. Kendall graduated in 2014, and Kylie followed in 2015. They attended Sierra Canyon School initially—Kylie was even on the cheerleading team—but the "normal" life didn't last long.
Kendall has mentioned that growing up with five older siblings meant she learned a lot by watching their mistakes. She saw the paparazzi frenzies and the public breakups before she was even a teenager. It's probably why she's the most private of the bunch today. She chose the "kidless freedom" and a house that isn't within walking distance of the rest of the family.
Why the "Younger" Era Still Matters
Looking back at Kendall and Kylie younger years isn't just a nostalgia trip. It’s a case study in how the "influencer" was born. They were the first generation to grow up entirely on camera and then use that platform to build legitimate, standalone businesses.
Kylie's rise wasn't just luck; it was a masterclass in identifying a personal "flaw" and branding it. Kendall’s career wasn't just about a famous last name; she had to prove herself in an industry that initially looked down on "reality stars" (Marc Jacobs and Karl Lagerfeld were early supporters who helped bridge that gap).
Steps for Navigating Their Legacy Today
If you're looking to understand the "Jenner Effect" or how they transitioned from tweens to moguls, here are the best ways to dive deeper:
- Watch the "Time Capsule" Episodes: Go back to Season 1 and Season 6 of KUWTK. The difference in their confidence and personal style is night and day.
- Analyze the Brand Shift: Compare their early PacSun designs with the "Kendall + Kylie" high-fashion line launched in 2016. It shows the evolution from "teen mall brand" to "Saks Fifth Avenue" luxury.
- Study the Social Media Pivot: Look at Kylie's 2014-2015 Instagram feed. This was the exact moment the "Instagram Face" aesthetic was popularized globally.
- Follow the Business Trajectory: Look into the 2020 Forbes "billionaire" controversy. It provides a more nuanced, realistic look at how celebrity wealth is reported versus the actual profitability of their companies like Kylie Cosmetics.
The reality is that Kendall and Kylie weren't just lucky kids. They were the first to turn a reality TV "side character" role into a primary seat at the table of global business and fashion. Whether you're a fan or not, you can't deny that the little girls fighting over the remote in 2007 ended up changing the way the entire world views fame.