There's one place on earth so influential in pop culture that Drake wrote a song about it and Kanye created a whole clothing line around its name. But this cultural mecca isn't a big city or an island destination, as some of West's fans believe. In fact, Calabasas is maybe the only place in the world that boasts as many Billboard artists as it does chain grocery stores. And while luxurious and nice — after all, its gated communities contain NBA players, Kardashians, and rappers along with dentists, lawyers, and agents — it’s also the string of strip malls and cul-de-sacs that make so many other American suburbs devoid of personality. But stars have decided to put their roots down in Calabasas. So that says something.

Driving around its roads, the suburb feels about as inspirational as a bottle of $5 water. So, does Calabasas deserve the style cred that it's earned? To find out more, we visited the town to uncover the roots of the Calabasas mythology, and find out why a seemingly cookie-cutter neighborhood is now synonymous with streetwear. With more horse trails than actual sidewalks and few stores to shop in, Calabasas has somehow ended up representing a new definition of luxury, one where access and finesse scores you more points than how much money you paid for it.

How did this place evolve from moms in red-bottomed heels to teenage girls in track suits and sneakers? What does it mean that Calabasas is a place where people end up after they've made it in their careers — and what does it offer for those who grow up within its borders, with every privilege and luxury in the world? Watch this episode of Style Out There and you tell us: Is Calabasas as cool as Kanye says it is?