Back in my nom-de-plume-tastic days as Dexter, I was once asked the following question:
Dear Dexter:Is there any kind of hat that goes with a formal-type coat that doesn’t look either silly or get you odd looks? The knitted-wool affair keeps my ears warm but doesn’t really go with the "knee-length coat and scarf" esthetic; the Fedora is still (mostly) out (and doesn’t keep your ears warm when it’s ten degrees outside). Any thoughts?
I don’t remember my answer (and the Advocate archives aren’t functioning quite properly at the moment), but happily, Glenn O’Brien, who’s the "style guy" for GQ, has recently answered just that very question, and with much greater expertise than I could ever bring (inhabiting an alter ego, as I did for about two years, gives you certain super powers, but one of them, alas, was not the ability to intuit the variety of hats available to the well-dressed man).
I encourage you to read (and view) the whole post, which is really a kind of tour-de-force. My favorite passage is this one:
Guys walking around in suits, hatless, on a freezing day may feel macho, but they look stupid. They look as stupid as the guys you see dressed that way trying to run between raindrops, maybe holding the Financial Times over their heads. Get with it, chumps! When it rains, you wear a raincoat and carry an umbrella. When it rains heavily, or snows, you wear boots or galoshes. If you don’t, you look stupid.
On chilly days in Midtown I often see men in suits, overcoats, and baseball caps. This looks preposterous, and it seems especially so if it’s a Yankees or a Mets cap. If it’s Titleist you just feel sad for the guy, and if it’s plain and non-adjustable and possibly heavy wool or leather, you think, “Well, he’s trying.” Trying, but failing.
There are several other natty alternatives—the touring cap, aka coppola; the golfer’s or newsboy cap; the deerstalker, aka “the Sherlock Holmes cap”, with a double brim and earflaps; the traditional Persian diplomat, which is often made of Persian lamb; and the similar Astrakhan or Politburo hat, the type favored by Brezhnev, Gorbachev, and other cold warriors.
Here are my fave three of the hat pictures Glenn posts. That’s Glenn in the two on the left, and his buddy Hooman on his right, wearing a Persian diplomat (the hat’s the diplomat, not Hooman, who’s a kind of jet-setting cosmopolite).
