Wit & Attitude Quote by P. J. O'Rourke

O'Rourke takes a tiny etiquette rule and inflates it into a demolition derby for masculinity, status, and the kind of performative decorum people mistake for character. The opening clause sounds like something your grandmother might approve of: take your hat off when greeting a lady. Then he yanks the rug out with that savage second half - leave it off for the rest of your life. The joke is structured like etiquette, but it runs on contempt for etiquette's emptier props.

The intent is less about millinery than about puncturing the idea that respectability can be purchased, worn, or signaled. Hats are a classic shorthand for trying to look like Someone: the fedora that says noir sophistication, the cowboy hat that says rugged authenticity, the baseball cap that says effortless cool. O'Rourke's punchline treats all of it as costume drama - a guy trying to edit himself in public, and failing.

Subtext: a lot of "politeness" is theater, but some theater is worse than none. He grants one narrow use for the hat: a brief, symbolic gesture of deference in a social ritual. Once the hat becomes permanent, it stops being manners and becomes branding. "Nothing looks more stupid than a hat" isn't an argument; it's a weaponized aesthetic judgment, the kind journalists deploy when they're really critiquing a class of people - strivers, poseurs, wannabe traditionalists - without naming them.

Context matters: O'Rourke's lane is political and cultural satire, written in the late-20th-century American key where suspicion of pretension is practically a civic religion. The hat, here, is just the funniest proxy for all the silly things we wear to convince strangers we're not silly.