The relationship between hip-hop and style goes back much further than the blogs informing us about what Kanye West or A$AP Rocky wore to some event last night do. For a burgeoning section of the style-inclined, who probably have more than a passing interest in hip-hop and rap, there's an endless supply of history lessons to be learned simply from watching old clips of Run DMC music videos or Yo! MTV Raps. But with the collision between the worlds of fashion and hip-hop becoming more and more visible by the day—Four Pins being a result of such cultural fusion, so to speak—Fresh Dressed, a documentary about just that topic, couldn't come out at a better time. As director Sacha Jenkins told me, "A film that explores a culture that was a reaction to oppression and lack of opportunity, fortunately and unfortunately because of the way things are going right now, lands at a good time because it's addressing the way young people feel."

As fans of both hip-hop and fashion, I'm sure we can all identify with and appreciate how the two worlds are interlaced. Fresh Dressed traces the evolution of hip-hop style all the way back to slavery and up through the gangs of The Bronx in the 1970s—a concept explored in another recent documentary, Rubble Kings—and the more daring and experimental present. Industry figures from both hip-hop and fashion, like Andre Leon Talley, Kanye West, Pharrell, Complex's own Marc Ecko and Noah Callahan-Bever and more, weigh in on how things have evolved over the past few decades and shaped the world around us.

For instance, in The Bronx in the '70s, gangs warred and the easiest way to identify gang members was by their customized jackets, often with defining gang symbols or emblems. But as hip-hop became more popular, gangs called truces on violence against each other and instead took to the basketball courts or dance floors to sort out their differences. This sparked a change in aesthetic from denim-clad warriors to the sweatsuit-wearing b-boys of the '80s.

But from the beginning and no matter the decade, at the core of the style-minded were always the tenets of self-expression and aspiration. We wear the things we do because we want to express who we are and who we want to be. This can clearly be seen in hip-hop's adoption of both Ralph Lauren and Tommy Hilfiger, two brands that stood for success that eventually became a measuring stick of wealth, spawning their own set of ardent followers in the process.

Elsewhere, local entrepreneurs championed their own style. Guys like Dapper Dan, who became famous for customizing clothing, often co-opting Louis Vuitton and Gucci logos until he was raided for copyright infringement, established a clear look by creating "blackenized" (Dan's words) designs. Small brands like Cross Colours blew up in part due to its presence on The Fresh Prince of Bel-Air and Karl Kani became the go-to wardrobe for 2Pac. Yet, the look was still labeled as "gang wear" until department stores appropriated the style as "streetwear," a much more palatable moniker for mass consumption. Almost immediately, the market became saturated. The competition to get into department stores was stiff with so many brands vying for the coveted retail space.

But as homegrown brands started up firmly inside the hip-hop community unlike, say, Ralph and Tommy, they did have a support system. Ventures from Russell Simmons (Phat Farm), Jay Z (Rocawear) and Daymond John (FUBU) all made big money in their heyday. Maybe most notably, Sean John completely broke through to the other side, bringing home the CFDA award for Menswear Designer of The Year in 2004. If you weren't aware, the Public School duo of Maxwell Osborne and Dao-Yi Chow, arguably menswear's hottest designers today, spent a good chunk of their careers at Sean John during this time.

Nowadays though, things seem to be waning in the opposite direction. In an age where Migos can launch a career off a song dedicated to Versace and Rocky and Kanye namedrop high-end brands endlessly, it's clear that hip-hop's fashion du jour has moved outside the culture. Granted, this movement truly speaks to the further integration of hip-hop and style as one. "Fashion and culture goes where the rappers go," Jenkins says. "The fashion vocabulary is expanding because rappers are going places they didn't go before and are being received in ways they hadn't before. A guy like Riccardo Tisci grew up with hip hop. For him to connect with rappers is exciting." Towards the tail end of Fresh Dressed, Swizz Beat even mentions that homosexuality and other once glaring cultural differences are now more accepted than ever as rappers are no longer afraid to experiment and really push the boundaries with their clothing.

While Fresh Dressed doesn't dive into some of the more subliminal issues of hip-hop and fashion's fusion—which would probably require the assistance of a few sociologists and anthropologists—it does provide a primer for anyone who wants to learn about the topic all in one place. "My hope is that the film will help educate some folks, young people in particular, and will open up a dialog about a lot of the bigger picture issues," Jenkins says. "Yet simultaneously, dressing cool is cool too. There's nothing wrong with that."

Fresh Dressed premiers in select theaters this Friday, June 26th, and is available for pre-order on Vimeo On Demand now.

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