One of the smartest ways to style out such a timeless menswear piece as a black blazer is to pair it with a dress shirt. Go off the beaten track and shake up your look by rounding off with a pair of black leather casual boots. Planning a pulled together look can be a bit of a juggling act on its own. Add subzero temps into the equation, and the whole thing becomes all the more difficult. Fear not, this here is your wintry outfit inspiration. More refined combos like this look well with silver hair.