You'll be surprised at how very easy it is for any gentleman to pull together this relaxed outfit. Just an olive quilted bomber jacket and tobacco cargo pants. To bring a little fanciness to this getup, introduce a pair of chelsea boots to the equation. If you're on a mission for an easy-to-transition look, you found it. This combination demonstrates that figuring out how to dress stylishly over 30 is not that daunting a task.