The question

I have always struggled to find a winter hat that is both dressy and warm. Are there any styles you can recommend?

The answer

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Dressy and warm are obvious requirements, but another, less obvious one is that the hat suit your face shape and personality.

While I have no way of determining these factors, I reached out to Karyn Gingras of Lilliput Hats in Toronto. Without much hesitation, she suggested the 1920s-style cloche as a versatile, flattering best bet. "They tend to come down over the ears, which makes them perfect for Canadian winters," she explained.

But what convinced me was this: "In fashion history, it's one of the only periods that [can be riffed on] without [making you look] like you're dressing in costume."

She recommends buying a hat made of natural fibres such as merino wool, boiled wool or rabbit-fur felt (which is brushed like angora and then felted). Alternatively, you could certainly add brooches or netting to dress up a beanie (as Jil Sander showed last year), but Gingras rightly notes that the cloche has structure and renewed relevance, in light of Downton Abbey and The Great Gatsby.

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Most of all, a cloche conveys an ineffable special-occasion spirit that is invaluable when braving winter's worst.

Amy Verner is The Globe and Mail's Paris-based style reporter. Have a fashion question? E-mail style@globeandmail.com. Follow her on Twitter: @amyverner.