Back when I was growing up in the 1970s my grandfather George Mason used to wear a dress hat on special occasions, or when he went into town. I always thought they looked cool, and probably tried them on from time to time. When I moved to Toronto in 1980, I noticed that older men were still wearing these hats. Perhaps took note of them and photographed them because of my grandfather.
I always assumed men wore dress hats, or “business hats” to hide balding heads, or to protect them from the elements. But it seems, in history, hats were a thing for other reasons. According to Deborah Henderson, a costume designer and the author of four books about men’s headwear, “Throughout history, people wore hats to indicate their social position in the world. Any trade—postman, engineer, pilot—had its own cap. Even lawyers, in the ’50s, all wore fedoras.”
Why did men stop wearing dress hats? An article from Esquire magazine suggests that nobody has pinpointed one sole reason why men stopped wearing hats. One reason could be the rise in automobile use. “With low roofs meaning you couldn’t wear a hat while driving and generally had no need to cover your head anyway, personal transport often negated the need for headwear.”
Another reason could be the stigma associated with WWII. “Another theory posited suggests that the hat suffered a serious decline after the end of World War II because it was an unwelcome reminder of the time people had spent in uniform. Men who fought did not want to wear hats with civilian clothes after the war.”
Benjamin Leszcz writes in Canadian Business, “A potent social signifier, hats identified a man’s role in society. (Hence the idiom of “putting one’s [insert profession] hat on.”) Little surprise, then, that the individualism of the ’60s and ’70s rejected the rule-bound world of hats, embracing anti-establishment afros, flowing locks and blow-dryer-enabled atrocities. By the late ’80s, the hat stigma faded, and every couple of years since, fashion journalists proclaim the hat’s comeback. Today, hats are runway stalwarts, and classic brands—like Borsalino, Stetson and Biltmore, which until recently was based in Guelph, Ont.—are holding steady. But hats will never entirely come back. The shift is decisive: historically, men wore hats to fit in; today, men wear hats to stand out.”
These days when I visit Toronto the people I see wearing dress hats are thirty-something hipsters going for that vintage look.
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