In preparation for founding Nylon, Ray Gun and Bikini publishers Marvin Scott Jarrett and Jaclynn Jarrett sold their majority interests in Ray Gun Publishing for an "undisclosed sum", then formed Pop Media. Nylon was co-founded in 1999 by the Jarretts, with ex-Ray Gun Editorial Director Mark Blackwell and supermodel Helena Christensen as Creative Director (no longer involved). According to Publisher Jaclynn Jarrett, the magazine's name was chosen because "...Marvin Scott Jarrett, our Editor-in-Chief, just liked the sound of Nylon. After picking it, we realized the New York/London tie-in, which is congruous with our editorial focus on these two cities." The design of the magazine was intended to be "hyper-legible", in answer to criticism of Ray-Gun 's "chaotic" layouts. The first issue was published on April 6, 1999....
The inaugural issue of Nylon was received with some disdain from Barry Didcock of the Glasgow Sunday Herald, who referred to Christensen's photography of Liv Tyler as "striking enough" but said her interview was "natter" and her photo/journal article about India was "gushing." He continued, "British music fans won't take much from Nylon they haven't already absorbed" from other magazines.
Medialife Magazine's Jennifer Cox wrote in 2001 that Nylon was "a little uppity, and it's not hard to understand why", describing it as "bold, idiosyncratic, challenging, absolutely of-the-moment," but unnoticed by "the mainstream" until March 2001, when Nylon was nominated for the ASME National Magazine award. She described the April issue as "groundbreaking" (for a fashion magazine) to feature an overweight woman in a history of women's weight, noted that the magazine's models "are more often interesting looking than beautiful per se." She found its photo spreads "bold with their use of white space and innovative photography" and noted Nylon's distinctive "heavy emphasis on music coverage "
