44 Best Winter Wedding Guest Dresses to Rock In Cold Weather Winter Style: How to wear a dress over a sweater Fashionblog Berlin 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 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