For a casually dapper outfit, dress in a white turtleneck and a white long sleeve shirt — these two pieces work really nice together. Why not take a more elegant approach with shoes and introduce a pair of black leather chelsea boots to your look? This one is a wonderful option when it comes to planning a cool outfit for awkward transition weather. Guys wondering how to wear smart outfits as you drift through your 20s, this getup should answer your question.