Mr. Guy, now 33, left hip-hop behind, both in his style and his soundtrack, but plenty of his generation didn’t, including Dao-Yi Chow of Public School and Ouigi Theodore of the Brooklyn Circus, two designers of more traditional men’s clothing still eager to preserve the hip-hop spirit of their younger years.

“It’s definitely a badge of honor, as well as one that you wear carefully,” said Mr. Chow, 38, who began his fashion career in marketing at Sean John, the label founded by Sean Combs. He told a story of a recent collaborative project in which he proposed including a five-panel cap, but was met with resistance, being told, “it feels a little too hip-hop.”

“There’s a negative connotation in the fashion world I’m in now, the CFDA world — after all these years they have some crazy idea that it’s still baggy jeans and big logos,” Mr. Chow said.