Pairing a military jacket with black chinos is an on-point pick for a relaxed yet dapper ensemble. Not sure how to finish off this getup? Finish off with brown chelsea boots to class it up. When it comes to dressing for in-between weather, nothing beats a neat ensemble that will keep you toasty and looking your best. This outfit shows that as a 20-year-old man, you have a wide range of sartorial options.