I bought this fun faux-chinchilla coat on end-of-season clearance last year; it's such a piece (of craziness, some would say) that I usually keep the rest of the outfit pretty simple. Easy substitutes here: exchange the t-shirt for a slouchy gray sweater (slouchiness is key! it must be somewhat oversized to balance out the leggings), or sub out the heels for Converse sneakers for a more casual look. Add a floppy fedora or a black baseball cap, and you're finished!
Coat: Ann Taylor // Pants: Kirna Zabete for Target* // T-shirt: Target // Heels: Ann Taylor // Clutch: Kenneth Cole // Watch: Michael Kors
* The side panels look almost purplish in this picture, but the pants are a true black in person.