Hylton was hired by "The New York Times Magazine" as a Contributing Writer in 2010. In October 2011, Hugo Lindgren, editor of "The New York Times Magazine", wrote, "By now you should know that when you see Wil's byline on a piece, it doesn't really matter what it's about. Just read it.” Hylton has written for the magazine about bioterrorism, the search for Air France Flight 447, the influence of "Breitbart News", and the prosecution of police officers after the death of Freddie Gray. His February 8, 2015 article about the family detention policy to imprison Central American women and children was cited by a federal judge in an injunction to suspend the policy two weeks later. His 2016 profile of the painter Chuck Close was a finalist for the "National Magazine Award" in Feature Writing.