Anyone who has read Jack London knows that cold weather can make a man do crazy things. But pairing an overcoat with a toboggan cap (even in all its boarding school nostalgia) is like sporting a backpack over a well-tailored suit. The wool crusher hat is a viable pompom-free option. A bit fuddy-duddy, yes, but as evidenced by compassionate conservatism and the Rolling Stones' A Bigger Bang tour, a little irony can go a long way toward making something old look new. So it goes with this season's take on the timeless topper. Worn low on the brow and with a certain je ne sais quoi, it's more Peter Sellers than Pete Doherty, and therefore more likely to attract a Britt Ekland, rather than a Kate Moss. For old-school originals, there are New York's Worth & Worth and London's Lock & Co. Hatters, which—true to its St. James's Street roots—has been crafting head-turning head warmers since 1676, and for the likes of Sir Winston Churchill and Frank Sinatra. In the new guard, Bottega Veneta gives camel wool a surprising edge, while Ferragamo does the same with navy, and J. Press keeps it classic in 100 percent Donegal wool. Crusher hats may have a fogy following, but at least they don't have earflaps.—LIZ MCDANIEL

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