A grey bomber jacket and a cable sweater are great menswear must-haves that will integrate nicely within your casual wardrobe. Introduce a pair of white and red canvas high top sneakers to the mix to keep the outfit fresh. On not-so-chilly days, you can work this summer-to-fall look and look absolutely amazing. Those who are curious whether you can still rock cool off-duty style as you get older, you have your answer.