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When you get out your winter running gear, don't put all your running shorts and short-sleeved tops too far out of sight. They work well as middle layers for cold winter days.
It's important not to overdress for winter running. Even if the temperature is in the teens, you will be surprised at how much you warm up after the first mile or two.
Everyone has a different tolerance for cold, and what is comfortable for your running buddy might be too warm or too cold for you. I have seen runners out in shorts in 20-degree weather, and that doesn't work for me. But when it is below 20, I will add a pair of shorts over my fleece tights to help keep the important parts more comfortable without adding more bulk. Similarly, try adding a short-sleeved shirt over a long-sleeved shirt to wear as a light extra layer under your winter running jacket.
If your hands tend to get cold, consider investing in some running mittens that have flip-back tops for ventilation. On very cold days, I'll wear my fleece gloves and then ball my hands into fists and pull them inside my jacket sleeves until I warm up (which usually takes about 2 miles if the temperature is below 20 degrees).
Finding the right layer combination takes some trial and error, but pay attention to what feels comfortable in different temperature ranges. You can even make a note in your running log, if you keep one, and you won't have to think as hard about what to wear.