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This has been a strange autumn so far. Temperatures haven’t dropped to appropriate December levels yet, and judging from the number of men wearing flip flops I’ve seen in the past few weeks, it’s lulling us into a false sense of security. You might be safe now, but New York weather is tricky and dump a foot of snow on you without a moment’s hesitation when you’re least expecting it.

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Thus, outerwear is something of a grey area right now. Can you get away with just a heavy sweater? Should you dust off your winter coat and resign yourself to the next five months of wearing it? Maybe you should just compromise by wearing a huge fur coat on top of a t-shirt with a fox on it. Maybe keep the trousers short, too. Accessorize all that with a dapper haircut and a pair of shiny leather loafers, and you’ll have an outfit that’s a perfect blend of vintage and contemporary, formal and casual. And modesty is overrated—go ahead and stick your nose in the air.

Follow The Art of Style by Kit Mills.  For more of Kit’s work, check out their website.

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