Pair a black blazer with dress pants for a really sharp getup. Bump up this outfit by rocking a pair of white canvas low top sneakers. During the colder months, when practicality is key, it can be easy to settle for a less-than-stylish outfit in the name of practicality. However, this outfit is a good illustration that you totally can stay comfy and remain stylish in the colder months. This combo is most probably what you're looking for as a 20-something guy.