For an outfit that's city-style-worthy and effortlessly sleek, choose a navy polo neck sweater and chinos. Puzzled as to how to finish? Complement your outfit with blue check canvas slip-on sneakers to mix things up a bit. So as you can see, it's very easy to look amazing and stay comfy come chillier weather, all thanks to looks like this one. With a look like this, any guy in his 50s is guaranteed to put most 20-somethings to shame.