For a casually cool outfit, team a black nylon bomber jacket with a navy crew-neck t-shirt — these two items play brilliantly together. If you're on the fence about how to finish off, introduce green check canvas slip-on sneakers to the mix. As you can see here, it's super easy to look dapper and stay warm when colder weather arrives, all thanks to combos like this. This combo should encourage anyone who wasn't sure about sporting casual outfits as a guy over 40.