This combo of a grey sweatshirt and a crew-neck t-shirt is proof that a safe casual outfit can still be really interesting. A pair of black athletic shoes will add a more laid-back aesthetic to the getup. During the colder months, when practicality is imperative, it can be easy to settle for a less-than-stylish outfit. This outfit, however, is a clear example that you can actually stay comfy and remain stylish at the same time in the colder months.