Kelly Osbourne has a coveted natural sense of style that draws heavily from her rock-n-roll lineage. So as the face of Madonna and daughter Lola’s Material Girl juniors clothing line for Macy’s, the lines are blurred between her own wardrobe and the brand’s new Fall 2011 collection.  Kelly claimed people on the set of a recent photo shoot for the Fall line didn’t even realize when she had changed out of her street clothes! “They’re like ‘it’s so much what you would wear,'” Kelly told Access Hollywood, adding, “so much of my style comes from, like, Madonna ’80s.” Like Kelly, the new Material Girl Fall looks exude fun but with an edgy rock-n-roll vibe. From a floral-printed dress toughened up with boots and a shearling jacket, to a T-shirt emblazoned with a black and white version of the United Kingdom flag, the line contains a multitude of pieces in which the rebellious star looks quite comfy.

During the NYC photoshoot, the Fashion Police co-host was all smiles in behind-the-scenes shots with the original Material Girl, Madonna, and her fashionable daughter, 14-year-old Lola.  The talented Lola co-designs the line and she was snapped with Kelly at some of NYC’s most recognizable landmarks, including the Empire State Building and on one of the Big Apple’s double-decker sightseeing buses. Look out for the ad campaign next month. Kelly’s flawless signature style often includes a pair of rockin’ cat-eye shades–like these from Tom Ford, available in three ultra-glam frame hues. –rpuccia

Buy these now: Tom Ford T0173, $232