20 Times Olivia Palermo Didn’t Play It Safe With Her Makeup — & It Paid Off

Okay, we’re just gonna say it: Olivia Palermo has never not looked good. Her fashion and beauty sense has always been impeccable, but she's been taking more and more risks lately — in large part due to her hairstylist Lacy Redway — and they're all paying off.

Back when she was a reality show cast member, she favored soft curls, pinky-nude lip color, and petal-pink blush. In fact, circa 2009, it seemed Palermo had never met a pink blush she didn’t love. It worked. It was pretty.

But in the past few years, Palermo has traded in her romantic, uptown-girl look for the more unexpected: statement lips in gothic shades, seafoam eyeshadow worn graphically, deconstructed braids. Palermo has gone badass — and we couldn't love it more. Ahead, see how the fashion plate and street style darling went from pretty to pretty edgy.