In 1990, the record label Tommy Boy Records bought 800 Carhartt jackets and had them embroidered with its logo, distributing them to "tastemakers" like Tupac and Dr. Dre, according to Esquire.
The label's Carhartt connection continued after it signed the group House of Pain, which wore Carhartt's Weathered Duck Detroit jacket in their music video for "Jump Around," according to The Detroit News.
The New York Times declared the mustard-brown and hunter-green Carhartt jacket the must-have outerwear for rappers and cool kids in New York City in the early '90s.
"In New York, hip-hoppers prefer their Carhartts mustard brown and hunter green with baggy corduroy pants stuffed into Timberland boots," The Times wrote.
According to The Times, Carhartt becoming a hip streetwear brand was due in large part to a new type of worker adopting the label's jackets as their uniform: drug dealers.
"They needed to keep warm and they needed to carry a lot of stuff," Steven Rapiel, Carhartt's New York City salesman, said in 1992. "Then the kids saw these guys on the street, and it became the hip thing to wear."