When the setting allows casual style, dress in a crew-neck sweater and black chinos. Feeling venturesome? Switch things up by wearing a pair of black casual boots. Putting together a standout outfit can be a bit of a juggling act on its own. Enter uncomfortably cold temps into the equation, and the whole thing becomes all the more difficult. No worries, this here is your winter outfit inspiration. So if you need outfit ideas on what to wear as you move into your 40s, this pairing is a good example.