Why not wear a black bomber jacket with black skinny jeans? As well as totally functional, both pieces look awesome together. And if you wish to easily up the ante of this outfit with one piece, complement this getup with a pair of dark brown suede casual boots. It's a viable idea when it comes to planning a neat getup for transeasonal weather. Those who are curious how to dress well as you pass the big 3-0, you have your answer.