My ears get cold really easily in the winter. Any wind at all when the temperature is under 55°F will feel like someone is jamming a sharpened icicle into my ear. And hats are always too thin, ride up, or look super goofy. I usually circumvent this with hoods, but sometimes they just make me look like too much like a juvenile delinquent. Got to maintain a low profile, ya know?
The answer is headbands. I made this one out of a turtleneck from an old sweater. I just cut it off and voilà: a thick, warm headband that pretty much stays in place and doesn't make me look shady.
I'm also wearing Keen boots, X2 jeans, Woolrich fleece, and a Wilson's leather jacket, to which I have added many pins and some pyramid studs.