For a look that's very straightforward but can be styled in a variety of different ways, wear a navy sweatshirt and dark brown chinos. A pair of low top sneakers can integrate wonderfully within a variety of combinations. As you can see, it's extremely easy to look on-trend and stay cozy when colder weather comes, all thanks to ensembles like this. Think it's hard for over-40 guys to nail edgy off-duty looks? This pairing will prove you otherwise.