For a casually dapper outfit, rock a windbreaker with khaki cargo pants — these items fit beautifully together. Complete this outfit with a pair of white high top sneakers to make the ensemble more practical. This getup is a viable idea when it comes to crafting a standout look for awkward fall weather. Those who are dubious whether you can still wear edgy casual looks as you get into your 50s, this getup should answer your question.