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Olivia Palermo's fashion career has been a short one so far, but she's been able to don more proverbial hats than most young girls who have lived in the limelight. Indeed, her public persona has ranged from the controversial, gossip-fodder socialite to reality TV super-villain to bonafide fashion inspiration. Today, Olivia Palermo runs an eponymous website with a staff, and also spreads her time knocking out some well-received collaborations (including her jewelry collection with Roberta Freymann that basically reignited our love for bib necklaces) and models for R29-approved brands like Tibi and Rochas. No matter how flawless her style is now, the journey to Perfect Outfit icon wasn't a short one. We've done some digging to unearth choice pics of Olivia from the past six years to map out the trajectory of one of our favorite style starlets.