Ashlee Simpson

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Uptown: Lia Sophia Industrielle II Collection Debut
Look: The 26-year-old actress and musician channels Edie Sedgwick with a pop in her platinum blond pixie, heavily-lined lids and peony pucker.

Downtown: Lucky Kids Magazine Launch
Look: Simpson parties with the tots in a brown fedora, choppy cropped 'do, grunge eye makeup and nude lips.