Picture this: You grow up in the south. You’re raised by a thrift-shopping mama and a science-minded (engineer) daddy. Sometimes you come home from school and rooms are painted different colors. You are a born creative and all paths lead to art school. You eventually move to L.A. and work on sets. You pay off student loans with money posing for Playboy and use the rest to start your interior design business. Before you know it, your take on whimsical mid-century modern takes flight. As they say, the rest is history. You became an icon in the boutique hotel world, creating your own brand, and riding each wave like the urban surfer you are. Behold, the long-reigning champ of whimsy and weird: Ms. Kelly Wearstler. Here are some inspired—yet doable—looks that pay homage to wild world of Wearstler.