Five years ago, Kylie Jenner was a high school student at Laurel Springs in Ojai, California and occasionally appeared on her family’s Keeping Up With the Kardashians reality show. Today, her media empire extends about as far as the eye can see.

The financial magazine Forbes recently estimated that Kylie’s net worth hovers somewhere around the $900 million mark, making her not just the richest member of the Kardashian-Jenner clan, but on course to become the youngest self-made billionaire ever.

Thanks to Keeping Up With the Kardashians, we’ve literally watched Kylie grow up before our very eyes and make many a fashion statement. From sassy tween to an all grown up twenty-year-old mom, she’s followed in the fashion forward footsteps of her sisters while forging a style identity all her own.

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And while her glam, red carpet looks are definitely something to behold, we love the out and about Kylie looks. Whether she’s shopping in Beverly Hills or slaying the concrete jungle in downtown Manhattan, Kylie can alternatively be cool, casual, or sleek and fleeked out.

“Over the last year, we’ve really seen Kylie transform into something larger than just another sister on Keeping Up With the Kardashians,” said social media commentator and style guru Lance Avalanche. “She’s become literally the single most important tastemaker and trendsetter. There’s really no one who comes close to her level of dominance at this point.”

And while Kylie’s star continues to rise and her billionaire ambitions make headlines, we’re just happy to take some serious style pointers from the fashionista.

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“What’s really cool about Kylie is that most of her street looks are not expensive,” said Avalanche. “She does it just like the rest of us, orders online, hits the mall, and looks good frequently on the cheap. She’s a girl after my own heart and pocketbook.”

In the spirt of looking good and saving a little cash, let’s take a look at our top ten favorite Kylie street looks and how she achieved them…