"...those boys couldn't hit the ground with their hats."
Adverts from Esquire Magazine (1956 - 1961)
My hat for 20 years
Looks like the inside of a coffin
Purchased in 1990 at Capper & Capper in Chicago
New York City may well be the last place on earth where a man can wear a hat to work. And by hat I mean a real hat. Something made of felt with a brim and sweatband. And if you're careful, it can be an anachronism but without costume, hipster vibe or diamond district ambiance.
The day I bought my hat was one of the coldest days I had, up to that point, lived through in my first ever Chicago winter. As I walked by Capper & Capper in the loop, I recalled some insane percentage of heat is lost through the head. I went in and bought this hat.
When my father-in-law saw my hat he told me a story of three men who flew to Chicago from New York in the early '50s. They were over served and, "When they got off the plane in Chicago those boys couldn't hit the ground with their hats."
The salesman monogrammed the band, I threw the feather away and wore it out while trying to keep the empty box in the shopping bag from tearing and blowing down Michigan Avenue. It's in decent shape thanks to being worn only a few days each winter but it's taken a slouched "noir" shape I'm proud of. It pairs well with a Polo coat or a single breasted rain coat.
Hat head can be avoided by using (here's where Dad has a laugh) hair gel. Once you take the hat off in your office you can comb your hair and hat head will disappear. But it works only once so going home or out will be an issue. As will finding a place to put it.
My hat has never been blocked or cleaned. And it probably should be although I'm hesitant for fear it will be screwed up forever. It's been banged around a bit and I never know where to keep it. There's no room in the box.