When you're dressing for a Winter run, think layers. Your body generates major heat when exercising, Dave said, so even though you might be freezing when you first step outside, there's a good chance you'll be hot by the end of your run. To find a balance, wear items you can pull off, such as a running vest or jacket and accessories like a hat or neck gaiter. (One POPSUGAR editor loves this lightweight, insulated jacket from Athleta.) "Stripped layers can be tied around your waist, carried, or dropped off at various check-points" during a loop route or an out-and-back, Dave said. One rule of thumb he shared: dress like the weather is 10-20 degrees warmer than it really is.