Dem Dare’s parties weren’t just local music events where guests could hear a new record from the afrocentric Native Tongues collective. The crew’s sense of style, which was reflected in Reggieknow’s popular flyers, defied stereotypes and showed attendees that the Dem Dare, or Darian, lifestyle presented a different path to success outside of the gangbangers who typically represented the streets of Chicago. “People thought we were nerds because we were eating right, drinking water, going to school, and talking about having goals. All we wanted to do was have the finer things in life,” says Disk Darian, a Dem Dare member who helped organize the parties and helped draw the graffiti letters on the flyers. Alongside East Coast hip-hop, Dem Dare was heavily inspired by popular Black Islamic movements like the Five-Percent Nation.
“Other hip-hop parties in Chicago were just full of angry dudes. The best thing I could say is that they were too ‘backpack.’ Parties where a cypher breaks out and there would be, like, three cyphers at once,” says Reggieknows’s close friend Wylie Styles, a fellow creative who frequented Dem Dare events and appreciated how the crew was inclusive towards women. “That crew was also so ill, fashion-wise, and Reg is the mastermind of that. But the ill part about Dem Dare was that it was also about Black excellence.”
Reggieknow drew characters wearing gear from Eddie Bauer, New Balance, Timberland, Nautica, Fila, and more. But Polo Ralph Lauren was the label he spotlighted the most. His illustrations flipped the brand’s country club image on its head, showing Black kids dipped in Polo grails like Stadium 1992 tanks tops, P-Wing cardigans, Hi-Tech ski jackets, and sit-down Bear knit sweaters. Los Angeles’ own Polo Don, Taz Arnold, who first met Reggie when he visited Chicago in 1992, distinctly remembered Reggieknow’s sense of style.
“He had the best dress sensibility in regards to wearing the clothes,” says Arnold, who notes that “Chicago’s Polo Don” looked fly in any brand. “He was telling people how to dress with those flyers, but he was the only one to attain that level out of his group. He grew up to look like his characters.”
There’s a video floating around the internet with a pre-College Dropout Kanye West getting his hair cut by Ibn Jasper and extolling the style virtues of Reggieknow, who he describes as “the God of Polo.” West recalls being stunned by how Reggieknow, a young Chicago cat with dreads, was able to afford $400 knit sweaters, gold fronts, and Cuban links in 1992 while everyone else, including himself, was putting $30 shirts on layaway. At one point he asks Jasper to stop cutting his hair so that he can properly emphasize how much he looked up to the “God of Chicago hip-hop.”
“This n***a walked by and I was like ‘Oh, shit!’ You would have thought you’ve seen a superstar! There goes Reginald!” exclaims West, who is grinning ear to ear and nearly losing his breath when speaking about Reggieknow. “I walked up to him, I had my Polo on, I just gave him a pound. Man, he gave me a pound and I was like: ‘Yeah, I know that n***a sees my Polo,” he says before breaking into laughter.
Although Dem Dare’s Polo fanaticism is frequently juxtaposed next to the Lo Lifes from Brooklyn, the luxurious look the Darians attained was not through boosting but through hard-earned dollars from actual careers, whether that meant DJing, throwing parties, or making Sprite commercials for Burrell. But despite how popular Dem Dare’s events became, not everyone applauded the crew. After the group got tired of the hate, the parties officially ended in 1994 and the Darians moved on to pursue their own personal endeavors.
“I think a lot of stories are told from New York’s and L.A.’s subcultures, but Dem Dare was ours,” says Abloh. “That Polo culture was an important movement that Reg spearheaded, and he developed the idea of Black kids in Polo with dreads. This is before the internet. Those flyers and the Dem Dare aesthetic, that was a fashion house to me.”
