To look smooth and stylish, team an olive blazer with dress pants. Balance out your look with more laid-back footwear, such as this pair of dark brown leather casual boots. Planning a pulled together outfit can be a bit of a juggling act on its own. Add below-freezing temps into the equation, and the whole thing becomes all the more difficult. Luckily, this here is your winter inspo. This pairing illustrates that figuring out fashion at age 40 is not that daunting a task.