Credit: Jamel Shabazz

The documentary Fresh Dressed, which premiered at the Sundance Film Festival in January and arrived in theaters Friday, presents a singular coming-of-age story: how hip-hop fashion was born, transcended its humbler-than-humble origins and grew up to remake street style into big business.

Directed by author-historian-journalist Sacha Jenkins, the movie traces hip-hop fashion from pre-Civil War days to the high-fashion runway. Starting with slavery, it charts the style movement’s progress through New York City’s bad old days of gang warfare, touching upon Run DMC’s “My Adidas,” Dapper Dan’s “blackenized” rip-offs of Gucci and Louis Vuitton to the department store infiltration of “urban” brands such as Karl Kani and Cross Colours. Fresh Dressed even includes a couple of scenes featuring a fresh-faced, pre-movie star Channing Tatum (in a stealth cameo mode) modeling the Sean John fashion line for CFDA winner Sean “Puffy” Combs in 2003s.

EW spoke to Jenkins about the style debt hip-hop owes to Hells Angels, about Kanye West’s world-beating fashion ambitions—he proclaims “being fresh is more important than having money” in the movie—and the culture of creating identity from struggle.

Entertainment Weekly: So why a documentary about hip-hop fashion? Of all aspects of the culture you could have focused on, why this one?

Sacha Jenkins: Because I’d already seen so many angles into telling the story of hip-hop. I figured it was a way to tell a story that was not only entertaining and true to the vitality of hip-hop, but also sort of dig into the social issues and the climate that created hip-hop and effected people who were ground zero for the birth of hip-hop culture.

Hip-hop fashion can be traced back to outlaw biker gangs?

In the late ‘60s/early ‘70s, in places like the South Bronx, the educational system was failing, there was white flight, landlords burning down buildings: it was the Wild West. Young people got together and formed gangs. The most iconic gang was the Hells Angels, who had a strong presence in New York City but also through films. Biker culture on celluloid helped spread this badass image. While a lot of these guys would have loved to have been in the Hells Angels, the truth of the matter is that they couldn’t be because they were black and Latino. But they saw what the biker groups were doing and thought it was cool. To identify and separate themselves, they started using the same aesthetic to create these jackets to symbolize their crew or their gang. But when [the gangs] declared a truce, the climate on the street changed. People started to look at you weird if you were wearing a gang jacket. And with this culture of dance, graffiti—hip-hop culture—it moved on to the self-styled customization of jean jackets. The gang lettering went onto being on sweatshirts with iron-on letters.

Clothes as a means to assert “otherness.”

It goes back beyond that to slavery and the idea of “Sunday Best.” It means you’re going to wear nice clothes to go to church. In slavery times, it meant that masters had to buy their slaves one nice outfit. When you consider that, Christianity wasn’t even part of what they were at that time, and in order to be a respectful worshipper in front of this new belief system, you’ve got to wear this style of clothing that’s not indigenous to who you are—it’s pretty heavy.

The movie also contains one of the more memorable Kanye West interviews in recent memory. He spends so much energy these days talking about fashion and how he wants to change the world. Not with music, but with fashion.

He talked about what he felt was lacking in the high fashion world and the general reluctance to let people like himself into that world. How determined he was to change the perception of those people and stand on his own two feet. For instance, he showed us his sneakers—the Adidas Yeezys that had yet to come out—and he had sketches and schematics and all these things. He was asking us really sincerely, “How much do you think these should cost? And what do you think of these?” Although he has very strong ideas about what he wants to do, he’s alo mindful of what people might want. He said, “Yo, I’m new to this but I’m really investing time in learning and understanding why things are important. I’m bringing my hip-hop essence and that energy into the high fashion world.”

For years, there have been certain signifiers in hip-hop fashion: baggy pants, sneakers, baseball caps. Nowadays, the look is skinny, designer, European. Help me trace hip-hop from where it’s been to where it’s going.

In the ‘80s, hip-hop fashion was about expressing yourself, becoming distinct. Through groups like Run DMC, it was broadcast around the world and people would take from it what they would. Run DMC’s style was Latin, in terms of its foundational influence. In the ‘90s, you have an industry being born. We’ve been taking all these things like we sample music—we sample classical, we sample heavy metal—to create something new. Sean “Puffy” Combs has won a CFDA award with Sean Jean. Hip-hop has made inroads into the world of high fashion and, more importantly, money. People were saying, “Hey, this Puffy guy is smart. Let’s do a vodka with him. Let’s transfer this hip-hop energy into products that go beyond music and clothing.” Once America embraced hip-hop on the financial and cultural side, it began to reach well beyond the inner city.

And into areas hip-hop music never reached.

Fashion is universal. It was easier for non hip-hop folk to grasp on and see the potential. A suburban kid could wear Fubu jeans. But a suburban kid couldn’t necessarily be NWA. Fashion is something you can touch. I think people feel more comfortable trying to dress like Ice Cube than trying to be Ice Cube. Hip-hop is not just people dancing and dressing cool. It comes from struggle. It comes from people who have a level of sophistication and creativity who were able to create a strong identity who gave them pride in who they were who made themselves attractive to millions of people around the world.