A tan blazer and charcoal dress pants are a classy outfit that every modern guy should have in his closet. Complete this getup with brown suede desert boots to give a touch of stylish effortlessness to this ensemble. Planning a pulled together combination can be a bit of a conundrum on its own. Enter uncomfortably cold temps into the equation, and the whole thing becomes even more difficult. Fear not, this here is your winter outfit inspiration. Wondering what you should wear as you go into your 40s? This outfit is a vivid example.