I used to read a bit of Mr. O'Rourke and enjoyed his less-political writings. As for headwear, I have a Barbour flatcap similar to the last you posted that I wear all fall, winter and into early spring. But now that it's finally getting consistently warmer around here I've been thinking about find a more lightweight alternative too keep my flowing locks from blowing in my face and to keep the sun out of my eyes.
Not the most helpful post, but I'll keep an eye on this thread for suggestions...