Despite a somewhat blemished history in the public eye, Ashlee Simpson has managed to shed indiscretions past and emerge an up-and-coming style maven with an edgy-meets-girlie look. The younger Simpson sis studied dance from an early age, and at eleven became the youngest student ever admitted to the prestigious School of American Ballet - my husband begged the question, “if she’s a professionally trained dancer, why was that awkward jig best she could come up with?”, but we’ll let bygones be bygones. These days, Ash is best known for her multi-layered black-on-black ensembles, which she keeps form being boring by playing with texture and unexpected accessories. To recreate her look, start with a pair of skinny black jeans (our favorite are Siwy Jeans Rose Drainpipe in Jet, available at Revolveclothing.com for $198 - use coupon code “JT” for 15% off your purchase) and a black hooded overcoat (we like the Horn Section Jacket at Anthropologie.com, $348). Add some patent booties (try the Type Z Voguish Bootie, $99.95 at Zappos.com) and fingerless gloves ($16, Urbanoutfitters.com) for a youthful edge, and finish off your look with smokey eyes and a side part sporting your hair’s natural texture. For those of you in warmer climes, you can accomplish the same look by swapping the overcoat for a chunky knit sweater of airy blouse - in black, of course!