Hip hop and fashion have always been intertwined. From Melle Mel wearing disco era leather suits to Run-DMC rapping about their Adidas to the backpack rappers of the 1990s all the way up to Jay Z opting for Tom Ford over popping molly. The timeline of hip hop is divided into style epochs the same way it is into musical ones. When you listen to a hip hop record, it’s easy to picture the outfit the rapper is wearing. The opposite is also true. Look at a picture of a rapper from a particular era, and the music from that time instantly comes flooding back.

Sacha Jenkins had seen the story of hip hop’s birth told many times over, but never through the lens of fashion, which is what prompted him to direct the documentary Fresh Dressed, which debuted to hyped reviews at Sundance and comes out in theaters and on demand June 26. The film speaks with some of the influencers and tastemakers who defined hip hop style through the years, such as Dapper Dan, Kanye West, and Pharrell Williams.

Fresh Dressed director Sacha Jenkins (Courtesy CNN)

Fresh Dressed director Sacha Jenkins (Courtesy CNN)

Jenkins is particularly well suited to tell this story. He grew up in New York City during the birth of hip hop and went on to become music editor at Vibe and a founder of the influential cultural magazine Ego Trip. In addition to directing, Jenkins is also the creative director of Mass Appeal, and served as a consultant on Cartoon Network’s The Boondocks, and is currently writing a book about the Beastie Boys with surviving members Ad Rock and Mike D.

Before the film’s New York City premiere, I had a chance to talk with Jenkins about the history of hip hop style, interviewing Kanye, and the deadstock sneakers he’d be wearing to the premiere.

What drew you to making this documentary?
Growing up in New York City. I moved here in 1977. My mother told me to go outside and play and I went outside with a Nerf football and everyone else had magic markers and there was music being played in the park and people were dancing. I was like what the hell is this? What that was would go on to be known as hip hop. I realized that the story [of hip hop] had been told a lot of different ways, but fashion would be a great platform to tell an even bigger story in terms of the environment that inspired hip hop. Fashion is a reflection of all of those things.

Who was the hardest interview to get for the movie?
Kanye. I didn’t even think I was going to get him. We were almost done and it was like a Tuesday and they were like can you go to Mexico tomorrow? So we went to Mexico. Somewhere really remote. He was with his family and his friends on this beautiful beach. He was there making music. I didn’t know what to expect. We had this conversation about fashion and he was engaged and on point and very thoughtful. And wanted to communicate these ideas about what fashion meant to him and how it made him feel and how it’s important to hip hop and how hip hop’s influence has influenced the way he sees fashion. He’s passionate about spreading that gospel in the world of high fashion.

What is the hip hop style that you most identify with? As an adult, I’m interested in not what people are wearing but why they are wearing it. For me, I learned through the film more about gang culture and how that influenced the fashion that came after. The idea of creating your own jacket that reflects your own personality and what you represent is really cool to me. After gang culture died down, crew culture [rose]—B-boys breakdancing, battling, iron-on letters on your shirt. That self-stylization mixed in with the sneakers, whether they’re shelltoe Adidas or suede Pumas, that to me is the most exciting.
Let me show you something. These are Pro-Keds, brand new, from the ‘70s. They’ve been in a box since the '70s. I’m wearing them tonight to the premiere, a deadstock pair of Pro-Keds 69ers. This is the sneaker that was worn by the original gang members and the original B-boys. I always say that fashion and hip hop is language. Back then, wearing this sneaker meant that you were cool. Even tonight, for those who know, when I put on my deadstock 1970s 69ers, that says something. And if you know what these are then you’re a part of the culture and the language that a few of us are really fluent in.
Everyone wants to look good and feel good and dress nice. That’s human. But on another level, it’s about identification. In the 80s, I could see someone dressed in a particular way and know that they were from Brooklyn or from Queens. Eventually that evolved into an industry, where folks who are of the culture are making clothing that specifically catered to these people. The idea of being “fresh dressed” was this idea of wearing stuff that’s fresh out of the box. In the inner city, even when you don’t have much, if you’re constantly wearing stuff that looks fresh out of the box, it says, well this guy must have money. In the '80s, so many kids that I came up with couldn’t afford to stay fresh, so what did they do? They sold crack to pay for that. So it’s 1987 and you’re 15 and you’re making $1,200 bucks a day selling crack, you can buy everyone in your building new sneakers. What does Kanye say in the film? “I just wanted money to stay fresh.” What does that say about the bigger picture? Why is there a group of people that ascribe so much power to clothing? Well, you’re talking about people that don’t have much.

Will the class struggle that promotes that attitude ever change?
The rappers are in a different place now. The film first starts out at slavery and the idea of Sunday best, which meant slaveowners had to buy their slaves a nice outfit for church. We go from slavery to gangs in the South Bronx. Those guys wanted to look like outlaw bikers but they couldn’t be a part of that society. Then this B-boy culture happened, and people are making their own clothes with iron-on letters. Then Dapper Dan happens, which is [a response] to these brands [like Gucci and Louis Vuitton] representing luxury but they aren’t speaking to us. So I’m going to take it and, like we do with everything else in hip hop, reimagine and remix it and add an attitude to it. In the music we sample everything and we sprinkle our attitude. Dapper Dan did the same thing with clothing. “Hey guys, this is the shit that rich white people wear, but I’m Dapper Dan and I’m going to introduce you to this world through my vision.” Then folks got a taste of that from looking at [Dapper Dan’s styles on] Eric B and Rakim’s album covers. Now they’re seeing these logos that they know mean something but they don’t really know what. After that, rappers launched their own brands. That got to the point where Jay Z owns Rocawear, but he’s not rapping about that, he’s rapping about Tom Ford. So everyone’s eyes go from here to there. The clothing is a reflection of where hip hop is and adapts. Now Jay Z is not in Marcy Projects. He’s in the sky somewhere rubbing elbows with other people in the sky. So his clothing is a reflection of that. But the kids in Marcy Projects are looking up to the sky. There’s nothing wrong with aspiration, but there has to be a level of reality between going from here to there.

The hip hop audience can be so fickle, does that mean we won’t see a hip hop clothing brand that lasts 100 years?
I think that hip hop fashion has been so tied into rappers. So the rappers’ career dictates the popularity of the clothing brands. If he’s not cool anymore why do I want to wear his stuff? If you’re talking about the core hip hop consumer, you’re talking about black and brown people in the inner city. Those people have been bred to be consumers. They have also been bred to look to the establishment for security and safety. So these brands that have been around for 100 years, they’re brands you can trust. Levi’s has been around since god knows when. You couldn’t have an African-American brand launch at the same time that Levi’s did for obvious reasons. Then flash forward to the '90s and 2000s where you have all of these urban brands launching and doing well. But now most of them are gone. Even Jay Z, you have your brand but you’re rapping about something else. What happened? My film doesn’t have the answers. But I wanted to present a conversation. My analogy is that high fashion is more about privilege, hip hop and urban fashion is more about survival.

Early B-boys (Photo by Jamel Shabazz)

Early B-boys (Photo by Jamel Shabazz)

How has the internet changed things?
Technology has made people more voyeurs than participants. When I was coming up I was different because I was a black kid and had a skateboard. I was into hip hop, into punk rock, into graffiti, and all these youth culture movements, Back then I could look at a skinhead who had a certain kind of laces in his boots and tell if he was a racist skinhead or if he was a non-racist skinhead. Nowadays kids from the inner city might dress like a skinhead or dress like a goth or have elements of goth mixed in with hip hop. It’s more of this knowing a little bit about everything. But the other way to look at it is, is that’s what hip hop is. Hip hop is sampling, taking lots of different things to create something new. Now the library you can sample as a person in the world of hip hop is much broader.

Is it strange to see kids hyped on retro Air Jordans, for example, when they don’t have the context from when those sneakers first came out?*
I think that the age that we came up in was the age of establishing the aesthetic value and cultural value of this stuff. Run-DMC wore Adidas and made a song about it and it resonated on such a large level. I came up at a time where we were out in the streets, playing, interacting. You’d come to the park with a new pair of sneakers and it was a big deal. Now you come to the Instagram with a new pair of sneakers. It’s this weird voyeuristic thing, where everyone is living in this kind of virtual world that’s about keeping up appearances. Don’t get me wrong, I’ve had these sneakers on ice for many years, but they’re extremely rare and tonight I’m wearing them at the premiere of my film which is about hip hop fashion. These were the founding fathers of hip hop footwear and that’s why I’m wearing them.

How did you get them?
This guy who’s a skater from Maryland, Chris Hall, became a sneaker nut, and I had a pair of sneakers hanging in my office that belonged to a friend that he really wanted. I called my friend and asked him if he wanted to sell them for $100, he was like O.K.. Chris was like thanks so much, man. I might have something for you. He pulled out this old beat-up box, and was like they’re for you. He came up on these in a basement in Brooklyn somewhere. I’ve had them for at least 10 years.

Where do you see hip hop fashion going?
It’s more about the attitude. There was that period when all the rappers had their brands and were doing really well. Now most of them are gone. What remains is Pharrell doing collaborations with people, Kanye doing collaborations, Swizz Beatz doing collaborations. I think outsiders realize that it’s about the energy and the spirit of hip hop. As long as that perspective is there, hip hop fashion will continue to evolve as people who have come from hip hop climb the ranks of the establishment or society. America has embraced hip hop the way it embraced rock n’ roll. Now that hip hop is part of the American fabric, pun intended, what stylistically comes from the hip hop mindset is gonna come from a broad cross-section of Americans. It’s not just the hood anymore. I can’t deny the white kid, who grew up his entire life listening to hip hop. I can’t say that he’s not hip hop. That energy has influenced the way he sees the world. If you’re from Iowa and a white kid who grew up with hip hop and you’re a designer, that energy is going to effect what it is that you create.

Justin Tejada is a writer and editor based in New York City. Follow him on Twitter at @just_tejada.