For an on-trend look without the need to sacrifice on comfort, we love this combination of a grey varsity jacket and tobacco chinos. And if you wish to easily smarten up your ensemble with a pair of shoes, introduce brown leather derby shoes to the equation. This outfit is a really good idea, especially for fall, when the temps are getting lower. As a 30-something Millennial guy, you probably want to start dressing like a grown-up. In this case, getups like this are a never-failing option.