This classic and casual pairing of a charcoal vertical striped suit and a tan v-neck sweater is extremely easy to put together without a second thought, helping you look amazing and prepared for anything without spending too much time searching through your wardrobe. Here's how to dress up this look: black leather dress boots. Putting together a pulled together ensemble can be a bit challenging on its own. Enter subzero temperatures into the equation, and the whole thing becomes all the more difficult. No worries, this here is your winter outfit inspiration. This is a good illustration of how to dress stylishly and look age-appropriate.