Kwijybow
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As Kent says, staying dry is most important, as moisture and cold is a ride killer. My general rule of thumb. low 50's - maybe a thin head covering, single layer up top hand coverings. low 40's - head covering, double layer on top, single layer on bottom, gloves, wool socks single layer. low 30's -head covering, jacket, double layer on top, single layer on bottom, gloves and liners, 2 layers thin wool socks, or regular shoes. low 20's and below - everything above, plus another base layer and usually a baclava. wind and water can make me drop down a notch despite temperature. base layers are usually the cheap polypropolene affairs at Academy or such. I like the Gecko Gear Ice tights, and wool socks, wool glove liners, cheap thinsulate glove shells. As pointed out before gloves and socks have to be loose fitting to allow circulation, false help to wear multiple layers and have them be too tight. My Gecko gear tights have held up over 8 seasons of winter commuting, and I probably need a new pair this year. Take Care, Nelson.
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