Putting together a grey vertical striped suit with a white dress shirt is an on-point idea for a smart and polished look. If you're hesitant about how to round off, introduce a pair of black leather dress boots to the mix. In the winter season, when comfort is above all, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. However, this outfit is a bright example that you totally can stay cozy and remain equally stylish during the winter season. As you can see here, after 40 you still have a wide range of styling options.