Just like her co-stars Blake Lively and Leighton Meester, Taylor Momsen has undergone quite the transformation since starring on Gossip Girl. She started out as the sweet, butter-wouldn’t-melt-in-her-mouth Jenny Humphrey, and over three years has swapped the cute designer frocks for a more provocative biker/rock chick getup. Together with the dark eye makeup and loooong hair extensions, this is a girl who wants the world to know that she’s, well, not a little girl anymore. But she still enjoys playing dress ups in big labels, whether it’s a moody lace dress from Dolce & Gabbana or dramatic thigh-high slit Versace. And Madonna obviously thinks she’s got style cred, since she chose her to be the face of her clothing line Material Girl. Now that she’s touring with her brand The Pretty Reckless, sporting some interesting stage wear to boot, we thought we’d take a trip down Miss Momsen memory lane...