The once ungentlemanly sneaker, it seems, has undergone a fashion baptism. The distinction between dress and athletic shoes is on the verge of collapse for fashion-forward men, as the humble gym shoe has outgrown its youth-culture/streetwear origins to become a fashion accessory, as well as a staple on runways, red carpets and in the workplace, where it is no longer considered the height of quirk to wear them with a suit.
He's probably still squinting in the bright sunlight of the 21st century, stroking his handlebar mustache, all, "Ahoy now! The future, I am in!"
With their historic ties to teen culture and hip-hop, sneakers connote youth and, in the context of the workplace, they are a swashbuckling statement that says: "I'm the new breed. I'm nimble afoot. I'm ready for revolution."
Like maybe the New York Times was the only paper still around today from the old-timey days that he came from, and that's why he decided to get a job writing for them.