A sweatshirt and black chinos are a nice go-to pairing to keep in your wardrobe. Breathe an added touch of sophistication into this look by rocking a pair of black derby shoes. During the winter months, when comfort is above all, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is a vivid example that you totally can stay toasty and remain equally stylish in the winter months. Perfect for a 20-something if you want to project a carefree image.