Combining a navy bomber jacket with black vertical striped chinos is a smart pick for a casual and cool ensemble. If you're puzzled as to how to round off, a pair of white leather low top sneakers is a smart idea. When temps are falling and fall is in the air, you'll love this outfit as your go-to for transitional weather. Those who are dubious whether you can still wear edgy casual outfits as you step into your 50s, you have your answer.