If you feel more confident wearing something functional, you'll like this dapper combo of a white crew-neck t-shirt and black chinos. When in doubt about what to wear in the footwear department, throw in black leather low top sneakers. In the colder months, when functionality is prized, it can be easy to settle for a less-than-stylish outfit. But this outfit is a striking example that you totally can stay warm and remain equally stylish during the colder months.