Okay Chicago, let's do this. Winter, the absurd season that strikes fear in the hearts and closets of Chi-town, has truly arrived. You had the chance to wear your cutest sweaters, trousers, and fun fingerless gloves in fall. That's like, so over, but you've still got the chance to show some style, we promise! Fight the urge to wrap up in a gazillion chunky knits and never leave the house again. There's a big, frozen world out there and we'll help you figure out what to wear to fight frost with fashion, all season long. For starters, we've found one smart, toasty warm, and (of course) completely cute outfit that will help you make a seamless change from fall to winter. Give these warm layers a try, then keep your creative coziness flowing for the next few months. If you get stuck, don't be scared (or house-bound). You've got us, and our styling skills, and we're not going anywhere.
Michael Kors Faux-Fur Vest Gilet, $321, available at Repertoire. MOTO Leigh Supersoft Jeans, $62.31, available at Topshop. Luv Aj Crystal Chunk Ring, $89.99, (originally $121), available at Need Supply. BB Dakota Channing Leather Jacket, $209, available at Revolve Clothing. Silk Rhea popover top, $110, available at J.Crew. Gianvito Rossi Court Shoes, $651.14, available at Browns.