Go for a refined ensemble in a blazer and a sweater vest. Complete this getup with a pair of dark brown leather derby shoes to pull the whole thing together. In the winter season, when warmth is essential, it can be easy to settle for a less-than-stylish outfit in the name of convenience. But this outfit is a good illustration that you totally can stay comfortable and remain equally stylish in the winter season. So if you're on the lookout for outfit ideas on what to wear as you move into your 40s, this combo is definitely worth saving for later.