This pairing of a polo neck sweater and white skinny jeans is on the casual side but will guarantee that you look dapper and incredibly sharp. Finishing off with dark brown loafers is a fail-safe way to breathe a sense of elegance into this outfit. During winter, when comfort is critical, it can be easy to settle for a less-than-stylish outfit in the name of practicality. However, this outfit is a vivid example that you can actually stay snug and remain stylish at the same time in winter. Men who are curious how to wear classic and casual style in your late 20s, this pairing should answer your question.