Sean John

The label that made the fashion establishment take a rapper's brand seriously. Sean Combs debuted Sean John in 1998 and launched it at Bloomingdale's a year later, and in 2004, after four straight nominations, he won the CFDA's Menswear Designer of the Year award, the industry's own seal of approval. That same year the brand was reported to be turning over around $400 million. Its later years were rockier: Combs bought the label back out of a bankruptcy in 2022 for about $7.5 million, and in October 2025 he was sentenced to 50 months in federal prison on prostitution-related convictions. Historically essential, but a hard name to buy into now.