Regular reader Marc Chevalier sends along his version of the proper way to wear a newsboy cap. He says it helps to have an authentic period cap: “The caps made in the ’20s and ’30s have a somewhat different shape from the ones made today. They’re more, well, sculptured.”
ladailymirror.com 
My Dad wore a newsboy cap while driving a T-Bird back in the early Sixties (to give you a mental picture). He was very cognizant of male haberdashery and wouldn’t have worn the hat in bad style. He wore it straight on his head, not tipped to the side. As Mr. Chevalier says, it was more flat than the 40’s newsboy hats. I guess every era has style codes that are a reaction to the previous era.
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@Lee Ann: A cap like that was essential if you had T-bird, an MG or Jaguar. 🙂
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Yep, cap shapes have changed over the decades, as have the ways of wearing them.
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