This contemporary combination of a black polo and brown sweatpants couldn't possibly come across other than devastatingly dapper. To bring some extra flair to your look, add low top sneakers to your ensemble. As you can see here, it's very easy to look on-trend and stay comfy when cooler days are here, all thanks to combinations like this one. Think it's hard for over-40 guys to master cool off-duty outfits? This pairing is irrefutable proof of otherwise.