Take your relaxed casual look up a notch in a tan hoodie and chinos. Balance out your outfit with more relaxed footwear, like this pair of navy athletic shoes. Crafting a pulled together ensemble can be a bit of a juggling act on its own. Add uncomfortably cold temps into the equation, and the whole thing becomes all the more difficult. Don't despair, this here is your wintry inspo. This outfit shows that as a 40-year-old man, you have a vast array of sartorial options.