That's because most men would rather freeze solid from the Adams apple up than wear a hat in winter. Maybe it's the toughness thing. We don't want to admit we feel the cold, even when we're down on our hands and knees looking in a snow bank for our ears. Maybe it's the goofy look of most winter hats, which is important since men are far more vain than women. That's a sign of weakness, not just poor judgment.
Poor judgment is something men long ago learned to live with.
I've seen a few Jester hats already this winter, but let's face it - unless you're a bike courier or entertaining royalty, you just look like a goof. It reminds me of a friend I had at university who wore one of those knit wool Sherpa hats all winter. It had the pointy top and long dangling earflaps. Probably as warm as anything, but he paid a terrible price. I don't remember a woman ever saying anything, but every man he knew razzed him something fierce.