How to Dress for Below Freezing Winter Weather KJP Women's Maple Lake Trail Long Sleeve Flannel Belted Maxi Dress Kiel James Patrick 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 Five tips to prepare for winter weather this holiday season