If you’re going to be skiing or taking a rigorous hike, then your body is going to generate a lot of heat. Though you still want insulated cold weather clothing to protect you, you will want to stay away from the heaviest insulation because you will become too warm and thick layers may restrict your body movements. You will also want a breathable material, like softshell jackets, that allow perspiration to evaporate. Moisture trapped against your body will cause you to feel much colder, even with a heavy jacket keeping the cold out. Therefore, both insulation and breathability should be your top considerations.
Temperatures between 20-40 degrees are hard to plan for if you are hiking for 5 miles. This is why layering may be very important. If temperatures are on the colder end of the spectrum, you may wear a non-insulated softshell jacket or a puffer jacket starting out, but then shed these for a fleece-lined base layer and long-sleeved shirt later in the day. Vests are very versatile as well since they help keep your core warm while allowing more airflow for optimal comfort.
Outdoor activities like ice fishing or camping may not require a lot of vigorous exertions that create body heat. If engaging in a less strenuous activity, choose winter outerwear that will provide the most protection from the elements, including wind and rain. Less movement also means that your movements will not be hampered by heavier materials. Consider a jacket or an overall bib combined with base layers for the most protection and comfort. Also think about a functional collar that you can pull up around the sensitive neck area as well as headwear.
Cold weather clothing is a necessity if you like to fish or ride your motorcycle year round. You may not engage in these activities when the temperature is below freezing, but consider that the longer you are exposed to even moderately cold temps or wind chills, the more uncomfortable you will be. If this is the case, choose winter outerwear that is rated for temperatures 10-20 degrees colder than the actual temperature. You may be a little warm at first, but after hours of exposure, you will be thankful for the extra warmth.
Remember to keep your intensity level in mind when you start looking for winter outerwear for sporting activities. The proof that you made the right or wrong choice will be reflected in how comfortable you are. After all, you want to focus on having fun rather than what you are wearing.