Avoid a mascot look by not going head-to-toe woolly. Grommeted leather under a topper puts the good girl/bad girl front and center, while matching gloves and kitten heels give it a retro spin.Coat: Mango, $160; mango.com.
Shell: Kate Spade Saturday, $220; saturday.com.
Skirt: BCBG Max Azria, $868; bcbg.com.
Clutch: Milly, $295; piperlime.com.
Gloves: Sermoneta Gloves, $300; sermonetagloves.com.
Kitten Heels: Raoul, $240; raoul.com.