Chicago Winter Packing List I think I'm getting the hang of this cold weather dressing thing! Here's what I'd pack for a visit to Chicago in the wintertime. This works for 44 Best Winter Wedding Guest Dresses to Rock In Cold Weather When temperatures dip, it is important to dress in layers to combat the cold. Prepare for extreme temperatures by dressing in layers and covering exposed skin. Synthetic fibers and wool are better KJP Women's Maple Lake Trail Long Sleeve Flannel Belted Maxi Dress Kiel James Patrick Burberry Check Wool Blend Chemisier Dress Autumn Winter Plaid Wool Dress for Women Spaghetti Strap Retro Party Vest Elegant Long Style