For a look that's smart and Bond-worthy, wear a navy vertical striped suit and a light blue dress shirt. Take your outfit a sportier path by rocking white canvas low top sneakers. So as you can see, it's super easy to look on-trend and stay toasty when colder weather comes, all thanks to outfits like this. This combination shows that figuring out how to dress well as a 30-something guy is totally doable.