About half of the staff here live in areas that experience winter; the other half don't see snow most years. The severity of your winter weather will influence which hat you'll need, but most of us should wear one once it starts to cool down. Even in moderate climates like Florida, a hat makes sense in December and January. If you're like me and lack hair on the top of your head, you'll be wearing a cap of some sort all winter long no matter where you live.
Keeping your head warm makes cold weather more bearable, and since ears and noses have lots of surface area and little blood flow, they tend to frost bite easily. Frozen flesh is dead and can get infected easily; if not prevented or treated, frostbite can lead to gangrene and eventually, death. A good hat will keep most of your head warm, which will keep the exposed parts a bit warmer.
The following list will go from least to most insulated, and I suggest you find one at least one level heavier than your normal weather wear. If the power is out or you are outside for extended periods gathering food and fuel, you'll need better gear than would normally get you through a day.
An actual watch cap is barely long enough to cover your eyes, while a beanie can often be pulled down over your entire face. I have both: the watch cap style is used as a base layer if needed, and the “cuff” of a beanie's extra length allows me to regulate how much of my ears and nape of neck are covered.
A side benefit of wearing a hat in the winter, especially following a disaster, is that bathing tends to become less frequent as people stop sweating every day. A hat will cover and restrain hair that hasn't been washed for a few days, which can reduce the amount of water you'll need to find and purify.
A few notes on materials:
Ball Cap
Any normal hat or cap is better than nothing, and a ball cap or cowboy hat will hold in some heat. If your winters are mild (no snow, light winds) this may be all you'll need.
Stocking Cap/Do-Rag
Actual stocking caps are made of the same material as nylon stockings. If you've never worn nylons, you'll not appreciate how much extra warmth they can provide. Living in the upper Midwest, our high school football players will often wear nylons under their uniforms to keep their legs warm during late season games. Do-rags and bandannas will cover your hair and let it provide a bit of natural insulation.
Scarf
A good, long scarf can be wrapped around the head and neck to hold in heat and keep out wind. You probably won't need the full Doctor Who 12 foot long scarf, but do get one that is made of material that will insulate.
Beanie/Toque/Watch Cap
Call them what you will, these are the most common and come in the widest variety of all the hats made. I personally don't care for the styles with the ball on top, but I have at least a dozen snug watch caps of varying materials and thicknesses to choose from in my cold weather gear. Late fall or early winter normally means a thin polyester cap, but as the weather gets colder I'll grab one that's a bit thicker and woven from thicker yarn. In January I'll wear either a wool cap or a polyester blend cap that has a Thinsulate liner in it. An actual watch cap is barely long enough to cover your eyes, while a beanie can often be pulled down over your entire face. I have both: the watch cap style is used as a base layer if needed, and the “cuff” of a beanie's extra length allows me to regulate how much of my ears and nape of neck are covered.
Fudd Hat
Hunting hats or surplus Army hats often have a wool liner that can be unfolded to cover the ears and upper neck. Great for keeping the snow off of your neck when traipsing through the woods, they vary in quality and insulation value. The TV show M.A.S.H. showed Radar wearing his hat with the ear flaps down when it was winter in Korea.
Balaclava
When wearing a hard hat (wind tends to blow up under the hat) or when the weather gets icy, it's time to break out the full-head-covering balaclava. Usually knit (although the newer fabrics are sewn), these will cover your entire head except for your face and extend below your chin to cover your neck. Great for being outside in the snow as it is falling or blowing about, they get warm very fast if you're exerting yourself at all.
Ski Mask
Similar to a balaclava, with the difference being that they also cover your face with openings for eyes, nostrils, and often mouths. Best worn when dealing with extreme cold and high winds; you may need to look into a set of goggles to go with it.
Hoods
A proper winter coat will have a hood that is insulated at least as well as the body of the coat is. True winter parkas come with coyote fur trim around the hood (artificial fur doesn't work, it holds water and will freeze) and a drawstring to keep it close to your face. Hoods are nice because they are easy to take off as needed, without losing them.A side benefit of wearing a hat in the winter, especially following a disaster, is that bathing tends to become less frequent as people stop sweating every day. A hat will cover and restrain hair that hasn't been washed for a few days, which can reduce the amount of water you'll need to find and purify.
- Cotton is the least insulting material for a hat. Good enough for a ball cap; avoid it in anything heavier.
- Polyester is a fair insulator, it matches wool for retaining heat (but only when dry) and is usually less bulky.
- Wool is the one rare material that will insulate even when wet, but it is heavy and many people find it too irritating (itchy) to wear.
- Polypropylene is one of the newer materials that wicks moisture and sweat away from your body, and it insulates quite well.
- Regardless of what material you choose, it is the air trapped in the weave or against your skin that does the real work of insulating you. A wider knit will trap larger pockets of air, but is also susceptible to losing those pockets of warmth to wind unless covered.
Bundle up.
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