This classic and casual pairing of a cardigan and a dress shirt is extremely easy to throw together in seconds time, helping you look dapper and prepared for anything without spending too much time rummaging through your closet. Balance out this ensemble with a more refined kind of footwear, such as this pair of dark brown leather dress boots. A great example of practical style, this outfit must be in your collection come winter season. Those who wonder how to wear classic and casual dressing in your 20s, you have your answer.