For a contemporary outfit without the need to sacrifice on functionality, we turn to this pairing of a red and black gingham long sleeve shirt and black ripped jeans. Change up this getup with a dressier kind of footwear, like this pair of black canvas low top sneakers. As you can see, it's super easy to look amazing and stay snug come fall, thanks to this look. Men who wonder how to pull off modern off-duty looks as you pass the big 3-0, this ensemble should answer your question.