For a cool and relaxed getup, opt for a varsity jacket and a grey hoodie — these two items work really good together. For a classier spin, why not complement your getup with black leather derby shoes? As you can see, this look is a really wonderful idea, especially for transitional weather, when the temperatures are falling. A perfect pairing to make you a well-dressed guy in his 20s, rather than just a guy in his 20s.