Pairing a black tank with grey plaid chinos is an on-point option for a casual ensemble. And if you wish to easily smarten up this outfit with footwear, add a pair of loafers to your look. When temps are dropping and fall is in the air, you'll appreciate how ideal this look is for in-between weather. Guys who wonder how to rock cool off-duty outfits as you make it through your 20s, you have your answer.