The weather is getting windy, chilly, and rainy in Chicago, and while my overcoat and trenchcoat are helping my body stay warm and dry, my head could use some protection as well. A beanie or baseball cap just wont do. And a paper boy makes me look like.... a boy. So I figure a fedora or a trilby should do the trick. What color should my first hat be? Should I try to match the color to my suits - which are mostly grey, navy, and brown? What if I'm wearing chalkstripes? Or should I match it to my coats - which are all black? Or should I match it to my shoes? Or is color pairing not really important with hats? Previous posts haven't said too much about this matter, and your comments would be greatly appreciated.