This casual combo of a beige crew-neck sweater and grey wool chinos comes in useful when you need to look sharp but have no extra time. Upgrade your ensemble with a pair of brown leather casual boots. In the colder months, when practicality is the priority, it can be easy to settle for a less-than-stylish getup in the name of functionality. This getup, however, is a vivid example that you can actually stay comfy and remain stylish at the same time in the colder months. This outfit illustrates how to succeed in smart dressing as a gent in his 20s.