A writer who famously despised hats also happened to wear them

“A hat should be taken off when you greet a lady and left off for the rest of your life. Nothing looks more stupid than a hat.”
— P.J. O’Rourke

Swimming first with the counterculture, P.J. O’Rourke drifted to the political right as a pundit, all the while retaining a sharp wit and no fear of kicking up some rhetorical dust.

One of his famous targets was, oddly, hats. Apart from the above (it’s from his 1983 book Modern Manners), he also thought that wearing a hat “implies that you are bald if you are a man and that your hair is dirty if you are a woman.”

Ouch.

He may have a point; I’m quite bald on the top, and I do like the variety of hats I’ve picked up over the years.

O’Rourke, who died at 74 in 2022 after battling lung cancer, may well have held one standard for the rest of us and another for himself. He was photographed wearing hats, like the time below:

He was also, you’ll note, also frequently photographed with a cigar.

I recall O’Rourke’s writing in magazines like Rolling Stone and Vanity Fair. I often got the impression he liked baiting his readers, annoying them as much as entertaining them.

And to that I will tip my favourite tweed hat (you can see me, um, rocking it here).