This off-duty combination of a charcoal wool bomber jacket and a black henley shirt is a real lifesaver when you need to look casually dapper but have no time to dress up. As for shoes, introduce white canvas low top sneakers to the mix. A perfect example of transitional style, this look is ideal come warmer weather. Those who are curious how to pull off cool off-duty looks as you go into your 30s, you have your answer.