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I love winter. There are those who flee to warm places, and there are others who follow the ski season. I have never been one for beaches, and I’m no good on a snowboard. My friend told me, “It’s like riding a skateboard,” but then I nearly broke my hip. At 38-years old, that would not be a good look.

Instead, I like Europe, and particularly Tuscany, in winter. It’s not bracingly cold – and growing up in Canada, I’ve had enough bracingly cold winters – nor is it some tropical resort to which I have no affinity or love. It’s a thinking-man’s kind of weather: frost in the mornings, giving way to brisk afternoons and cool evenings that make a warm fire inviting, but not so cold that going out for dinner is a chore.

Thus, for a thinking-man’s winter, here are just enough clothing options (socks and underwear excluded) to last you a weekend in a place like Florence, Italy – just make sure to go before or after the madness of the Pitti shows.
Let’s start with a jacket. Giorgio Armani said that this was the foundation of a man’s wardrobe, and, while you can debate this, for a winter vacation you are going to need a proper cover-up. Quilted jackets and double breasted jackets are both on trend right now, but they don’t always come together as well as the Veneto double-breasted sportsjacket from Epaulet ($1200) in quilted wool. Also, it will fulfill the tiresome “jacket required” rules if you absolutely have to patronize such an establishment.

For her, the Japanese company Nooy makes a beautiful and delicate “Bird jacket” available at Modern Appealing Clothing in San Francisco, $945.
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