This casual combo of a navy varsity jacket and navy cargo pants is a surefire option when you need to look dapper but have no time. To introduce a hint of stylish effortlessness to this look, complete this getup with a pair of white and red athletic shoes. When it comes to dressing for awkward fall weather, nothing beats a cool combo that can take you from season to season. Gents who wonder how to dress well and look good as you make it through your 20s, you have your answer.