Such must-haves as a field jacket and navy patchwork jeans are an easy way to inject effortless cool into your casual styling lineup. If you need to immediately smarten up this look with a pair of shoes, complement your ensemble with tan chelsea boots. As you can see, this combo is a really smart choice, especially for summer-to-fall weather, when the mercury is starting to drop. Guys wondering how to wear semi-casual dressing as you move through your 20s, this getup should answer your question.